DR ANTHONY MELVIN CRASTO,WorldDrugTracker, helping millions, A 90 % paralysed man in action for you, I am suffering from transverse mylitis and bound to a wheel chair, With death on the horizon, nothing will not stop me except God................DR ANTHONY MELVIN CRASTO Ph.D ( ICT, Mumbai) , INDIA 25Yrs Exp. in the feld of Organic Chemistry,Working for GLENMARK GENERICS at Navi Mumbai, INDIA. Serving chemists around the world. Helping them with websites on Chemistry.Million hits on google, world acclamation from industry, academia, drug authorities for websites, blogs and educational contribution

Saturday 18 January 2014

Nitrilotriacetic Acid Anhydride,1H NMR AND 13C NMR

NTA

learn nmr the simple way with simple molecules, two-four signals at a time with examples

PROTON NMR

1H(d6-acetone, 400 MHz): 

3.920(s, 4H), 
The two PLUS two  NCH2 protons of -NCH2-C=O-O on the ring

3.620(s, 2H); 

The two   NCH2 protons of -NCH2-C=O-OH on side chain


CARBON 13 NMR


13C(d6-acetone, 100 MHz): 

171.18, The single carbonyl carbon  of -NCH2-C=O-OH on side chain

165.51(2C),  The two  carbonyl carbons  of -NCH2-C=O- on the ring

54.79, The single N attached carbon  of -NCH2-C=O-OH on side chain

52.54(2C), The two N attached Carbons at   -NCH2-C=O-O on the ring

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ANTHONY MELVIN CRASTO
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Tuesday 14 January 2014

MIDOSTAURIN MP


MIDOSTAURIN
https://www.google.co.in/patents/US5093330
EXAMPLE 18 N-benzoyl-staurosporine

0.035 ml (0.3 mmol) of benzoyl chloride is added at room temperature to a solution of 116.5 mg (0.25 mmol) of staurosporine and 0.065 ml (0.38 mmol) of N,N-diisopropylethylamine in 2 ml of chloroform and the whole is stirred for 10 minutes. The reaction mixture is diluted with chloroform, washed with sodium bicarbonate solution, dried over magnesium sulphate and concentrated by evaporation. The crude product is chromatographed on silica gel (eluant:methylene chloride/ethanol 30:1); m.p. 235


SEE FULL REPORT ON
http://www.allfordrugs.com/2014/01/14/midostaurin-with-potential-antiangiogenic-and-antineoplastic-activities/

IDELALISIB NMR


An antineoplastic agent and p110delta inhibitor
Icos (Originator)
  • CAL-101
  • GS-1101
  • Idelalisib
  • UNII-YG57I8T5M0
M.Wt: 415.43
Formula: C22H18FN7O
CAS No.: 870281-82-6
CAL-101 Solubility: DMSO ≥80mg/mL Water <1.2mg/mL Ethanol ≥33mg/mL
5-Fluoro-3-phenyl-2-[(1S)-1-(7H-purin-6-ylamino)propyl]-4(3H)-quinazolinone
 WO2005113556A1
compound 107 idelalisib as a light yellow solid (7.2 g, 50%).
1H NMR (300 MHz, 80 0C, DMSO-d5) δ 12.66 (broad s, IH), 8.11 (s, IH), 8.02 (broad s, IH), 7.81-7.73 (m, IH),7.60-7.42 (m, 6H), 7.25-7.15 (m, 2H), 4.97 (broad s, IH), 2.02-1.73 (m, 2H), 0.79 (t, J= 7.3 Hz, 3H).
ESI-MS m/z 416.2 (MH+).
C, H, N elemental analysis (C22Hi8N7OF-EtOH- 0.4 H2O).
Chiral purity 99.8:0.2 (S:R) using chiral HPLC (4.6 x 250 mm Chiralpak ODH column, 20 °C, 85:15 hexanes : EtOH, 1 rnL/min, sample loaded at a concentration of 1 mg/mL in EtOH) . The reaction described above and compound 107 idelalisib are shown below.
Figure imgf000155_0001
The synthesis of a compound in accordance with formula I is first exemplified using steps A-E below, which provide a synthetic procedure for compound 107, the structure of which is shown below.
Figure imgf000150_0001
(107) is idelalisib
.................
READ AT
 http://newdrugapprovals.wordpress.com/2014/01/14/idelalisib-us-fda-accepts-nda-for-gileads-idelalisib-for-the-treatment-of-refractory-indolent-non-hodgkins-lymphoma/

Friday 10 January 2014

2,4,6-Trichlorophenyl 3,4-Dihydronaphthalene-2-Carboxylate, NMR, IR, MASS









LEARN SPECTROSCOPY THE PRACTICAL WAY WITH EXAMPLES

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 2,4,6-Trichlorophenyl 3,4-Dihydronaphthalene-2-Carboxylate (7

showed the following characterization data: mp 80–82 °C; Rf = 0.57 (hexane/EtOAc 9/1); 

1H NMR (400 MHz, CDCl3)
 δ: 2.76 (t, J = 7.9 Hz, 2 H), 2.97 (t, J = 8.3 Hz, 2H), 7.20 – 7.35 (m, 4 H), 7.40 (s, 2 H), 7.86 (s, 1H). 

The two -CH2- protons at dihydonapthalene ring appear at 2.76 and 2.97 as triplets

Links
see1H NMR pdf


13C NMR (100 MHz, CDCl3
δ: 22.2, 27.4, 126.7, 126.9, 127.8, 128.5, 129.0, 129.8, 130.3, 131.8, 132.0, 137.2, 139.9, 143.3, 163.5.

The two -C- CARBONS on  dihydonapthalene ring appear at 22.2 and 27.2

Links


see 13C NMR pdf
 IR (ATR, neat)
 cm-1: 1733 C=0, 1624, 1564, 1448, 1380, 1275, 1238, 1201, 1184, 1171, 1022, 958, 855, 757, 737, 714.

 HRMS (EI): m/z calcd for C17H12Cl3O2[M+H+] 352.9897, found 352.9896.


 Elemental Analysis: Anal. Calcd. for C17H11Cl3O2: C, 57.74; H, 3.14. Found: C, 57.72; H, 3.08.


CHECK OUT A 19F NMR BELOW FOR COMPD 2



 3,4-Dihydronaphthalen-2-yl trifluoromethanesulfonate (2) showed the following characterization data: Rf = 0.63 (hexane/EtOAc 9/1); 

1H NMR pdf(400 MHz, CDCl3) δ: 2.70 (t, J = 8.4 Hz, 2 H), 3.06 (t, J = 8.2 Hz, 2 H), 6.48 (s, 1 H), 7.05 – 7.10 (m, 1 H), 7.12 – 7.16 (m, 1 H), 7.17 – 7.23 (m, 2 H). 


13C NMR pdf(100 MHz, CDCl3) δ: 26.5, 28.5, 118.5, 118.5 (q, 1JCF = 320.7 Hz), 127.3, 127.5, 128.4, 131.1, 132.9, 149.9. 


19F NMR pdf(376 MHz, CDCl3) δ: –73.6.   ONE SIGNAL SEEN
Links

IR (ATR, neat) cm-1: 1664, 1416, 1248, 1202, 1137, 1062, 985, 895, 824, 753, 610. 


HMRS (EI): m/z calcd for C11H9F3O3S [M+] 278.0219, found 278.0222. 


Elemental Analysis: Anal. Calcd. for C11H9F3O3S: C, 47.48; H, 3.26. Found: C, 47.27; H, 3.19. 






2,4,6-Trichlorophenyl formate (6) showed the following characterization data: mp 72–73 °C; Rf = 0.57 (hexane/EtOAc 9/1); 

1H NMR pdf(400 MHz, CDCl3) δ: 7.41 (s, 2 H), 8.28 (s, 1 H).

 13C NMR pdf(100 MHz, CDCl3) δ: 128.7, 129.2, 132.6, 141.9, 156.2.


 IR (ATR, neat) cm-1: 3078, 1732 C=O, 1563, 1447, 1385, 1227, 1085, 1057, 850, 820, 805, 678, 562. 

HRMS (ESI-TOF): m/z calcd for C7H3Cl3O2 [M+] 223.9194, found 223.9190. 


Elemental Analysis: Anal. Calcd. for C7H3Cl3O2: C, 37.29; H, 1.34. Found: C, 37.10; H, 1.40.




om  animation

DAPAGLIFLOZIN

DAPAGLIFLOZIN, BMS-512148
READ AT
(2S,3R,4R,5S,6R)-2-[4-chloro-3-(4-ethoxybenzyl)phenyl]-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol,
cas 461432-26-8
Molecular Formula: C21H25ClO6
Molecular Weight: 408.87

Bristol-Myers Squibb (Originator)
AstraZeneca
TYPE 2 DIABETES,SGLT-2 Inhibitors
launched 2012,  as forxiga in EU
Figure US20120282336A1-20121108-C00006
Dapagliflozin propanediol is a solvate containing 1:1:1 ratio of the dapagliflozin, (S)-(+)-1,2-propanediol, and water.

..........................................................................
PATENTS
WO 2010138535
WO 2011060256
WO 2012041898
WO 2012163990
WO 2013068850
WO 2012163546
WO 2013068850
WO 2013079501
Dapagliflozin (INN/USAN,[1] trade name Forxiga) is a drug used to treat type 2 diabetes. It was developed by Bristol-Myers Squibb in partnership with AstraZeneca. Although dapagliflozin's method of action would operate on both types of diabetes[1] and other conditions resulting inhyperglycemia, the current clinical trials specifically exclude participants with type 1 diabetes.[2][3]
In July 2011 an US Food and Drug Administration (FDA) committee recommended against approval until more data was available.[4] The Prescription Drug User Fee Act (PDUFA) date for dapagliflozin for the treatment of Type 2 diabetes was extended three months by the FDA to January 28, 2012.
In April 2012, the Committee for Medicinal Products for Human Use (CHMP) of the European Medicines Agency issued a positive opinion on the drug. It is now marketed in a number of European countries including the UK and Germany.

The IC50 for SGLT2 is less than one thousandth of the IC50 for SGLT1 (1.1 versus 1390 nmol/l), so that the drug does not interfere with the intestinal glucose absorption.[7]

  1.  Statement on a nonproprietory name adopted by the USAN council
  2.  Efficacy and Safety of Dapagliflozin, Added to Therapy of Patients With Type 2 Diabetes With Inadequate Glycemic Control on Insulin, ClinicalTrials.gov, April 2009
  3.  Trial Details for Trial MB102-020, Bristol-Myers Squibb, May 2009
  4.  "FDA panel advises against approval of dapagliflozin". 19 July 2011.
  5.  Prous Science: Molecule of the Month November 2007
  6.  UEndocrine: Internet Endocrinology Community
  7.  Schubert-Zsilavecz, M, Wurglics, M, Neue Arzneimittel 2008/2009
  8. more
    1) Pal, Manojit et al; Improved Process for the preparation of SGLT2 inhibitor dapagliflozin via glycosylation of 5-bromo-2-Chloro-4'-ethoxydiphenylmethane with Gluconolactone ;. Indian Pat Appl,. 2010CH03942 , 19 Oct 2012
    2) Lemaire, Sebastien et al; Stereoselective C-Glycosylation Reactions with Arylzinc Reagents ;Organic Letters , 2012, 14 (6), 1480-1483;
    3) Zhuo, Biqin and Xing, Xijuan; Process for preparation of Dapagliflozin amino acid cocrystals ;Faming Zhuanli Shenqing , 102 167 715, 31 Aug 2011
    4) Shao, Hua et al; Total synthesis of SGLT2 inhibitor Dapagliflozin ; Hecheng Huaxue , 18 (3), 389-392; 2010
    5) Liou, Jason et al; Processes for the preparation of C-Aryl glycoside amino acid complexes as potential SGLT2 Inhibitors ;. PCT Int Appl,. WO2010022313
    6) Seed, Brian et al; Preparation of Deuterated benzyl-benzene glycosides having an inhibitory Effect on sodium-dependent glucose co-transporter; . PCT Int Appl,. WO2010009243
    7) Song, Yanli et al; Preparation of benzylbenzene glycoside Derivatives as antidiabetic Agents ;. PCT Int Appl,. WO2009026537
    8) Meng, Wei et al; D iscovery of Dapagliflozin: A Potent, Selective Renal Sodium-Dependent Glucose cotransporter 2 (SGLT2) Inhibitor for the Treatment of Type 2 Diabetes ; Journal of Medicinal chemistr y, 2008, 51 (5), 1145 -1149;
    9) Gougoutas, Jack Z. et al; Solvates Crystalline complexes of amino acid with (1S)-1 ,5-anhydro-LC (3 - ((phenyl) methyl) phenyl)-D-glucitol were prepared as for SGLT2 Inhibitors the treatment of Diabetes ;. PCT Int Appl,. WO2008002824
    10) Deshpande, Prashant P. et al; Methods of producing C-Aryl glucoside SGLT2 Inhibitors ;.. U.S. Pat Appl Publ,. 20,040,138,439
     as hyperglycemia, hyperinsulinemia, obesity, hypertriglyceridemia, Syndrome X, diabetic
....................................

In Vitro Characterization and Pharmacokinetics of Dapagliflozin ...

dmd.aspetjournals.org/content/.../DMD29165_supplemental_data_.doc

Dapagliflozin (BMS-512148), (2S,3R,4R,5S,6R)-2-(3-(4-Ethoxybenzyl)-4-chlorophenyl)
-6-hydroxymethyl-tetrahydro-2H-pyran-3,4,5-triol. 1H NMR (500 MHz, CD3OD) δ 7.33
(d, J = 6.0, 1H), 7.31 (d, J = 2.2, 1H), 7.31 (dd, J = 2.2, 6.0, 1H), 7.07 (d, J = 8.8, 2H),
6.78 (d, J = 8.8, 2H), 4.07-3.90 (m, 7H), 3.85 (d, J = 10.6, 1H), 3.69 (dd, J = 5.3, 10.6,
1H), 3.42-3.25 (m, 4H), 1.34 (t, J = 7.0, 3H). 13C NMR (125 MHz, CD3OD) δ 158.8,
140.0, 139.9, 134.4, 132.9, 131.9, 130.8, 130.1, 128.2, 115.5, 82.9, 82.2, 79.7, 76.4, 71.9,
64.5, 63.1, 39.2, 15.2.
HRMS calculated for C21H25ClNaO6 (M+Na)+
For C21H25ClO6: C, 61.68; H, 6.16. Found: C, 61.16; H, 6.58.
: 431.1237; found 431.1234. Anal. Calcd
SECOND SET
J. Med. Chem., 2008, 51 (5), pp 1145–1149
DOI: 10.1021/jm701272q
1H NMR (500 MHz, CD3OD) δ 7.33 (d, J = 6.0, 1H), 7.31 (d, J = 2.2, 1H), 7.31 (dd, J = 2.2, 6.0, 1H), 7.07 (d, J = 8.8, 2H), 6.78 (d, J = 8.8, 2H), 4.07–3.90 (m, 7H), 3.85 (d, J = 10.6, 1H), 3.69 (dd, J = 5.3, 10.6, 1H), 3.42–3.25 (m, 4H), 1.34 (t, J = 7.0, 3H);
13C NMR (125 MHz, CD3OD) δ 158.8, 140.0, 139.9, 134.4, 132.9, 131.9, 130.8, 130.1, 128.2, 115.5, 82.9, 82.2, 79.7, 76.4, 71.9, 64.5, 63.1, 39.2, 15.2;
HRMS calcd for C21H25ClNaO6 (M + Na)+ 431.1237, found 431.1234. Anal. Calcd for C21H25ClO6: C, 61.68; H, 6.16. Found: C, 61.16; H, 6.58.
...........................
HPLC
  • HPLC measurements were performed with an Agilent 1100 series instrument equipped with a UV-vis detector set to 240 nm according to the following method:
    Column: Ascentis Express RP-Amide 4.6 x 150 mm, 2.7 mm;
    Column temperature: 25 °C
    - Eluent A: 0.1 % formic acid in water
    - Eluent B: 0.1 % formic acid in acetonitrile
    - Injection volume: 3 mL
    - Flow: 0.7 mL/min
    - Gradient:
    Time [min][%] B
    0.025
    25.065
    26.070
    29.070
    29.525
    35.025
    ..........................
     http://www.google.com/patents/WO2013068850A2?cl=en

     EXAMPLE 24 - Synthesis of 2,4-di-6>-ieri-butyldiphenylsilyl-l-C-(4-chloro-3-(4- ethoxybenzyl)phenyl)- -D-glucopyranoside 2,4-di-6>-TBDPS-dapagliflozin; (IVj"))

    [0229] l-(5-Bromo-2-chlorobenzyl)-4-ethoxybenzene (1.5 g, 4.6 mmol) and magnesium powder (0.54 g, 22.2 mmol) were placed in a suitable reactor, followed by THF (12 mL) and 1,2- dibromoethane (0.16 mL). The mixture was heated to reflux. After the reaction had initiated, a solution of l-(5-bromo-2-chlorobenzyl)-4-ethoxybenzene (4.5 g, 13.8 mmol) in THF (28 mL) was added dropwise. The mixture was allowed to stir for another hour under reflux, and was then cooled to ambient temperature, and then titrated to determine the concentration. The above prepared 4-chloro-3-[(4-ethoxyphenyl)methyl]phenyl magnesium bromide (31 mL, 10 mmol, 0.32 M in THF) and A1C13 (0.5 M in THF, 8.0 mL, 4.0 mmol) were mixed at ambient temperature to give a black solution, which was stirred at ambient temperature for 1 hour. To a solution of
    I, 6-anhydro-2,4-di-6>-ieri-butyldiphenylsilyl- -D-glucopyranose (0.64 g, 1.0 mmol) in PhOMe (3.0 mL) at ambient temperature was added phenylmagnesium bromide (0.38 mL, 1.0 mmol, 2.6 M solution in Et20). After stirring for about 5 min the solution was then added into the above prepared aluminum mixture via syringe, followed by additional PhOMe (1.0 mL) to rinse the flask. The mixture was concentrated under reduced pressure (50 torr) at 60 °C (external bath temperature) to remove low-boiling point ethereal solvents and then PhOMe (6mL) was added. The reaction mixture was heated at 130 °C (external bath temperature) for 8 hours at which time HPLC assay analysis indicated a 51% yield of 2,4-di-6>-ieri-butyldiphenylsilyl-l-C-(4-chloro-3- (4-ethoxybenzyl)phenyl)- -D-glucopyranoside. After cooling to ambient temperature, the reaction was treated with 10% aqueous NaOH (1 mL), THF (10 mL) and diatomaceous earth at ambient temperature, then the mixture was filtered and the filter cake was washed with THF. The combined filtrates were concentrated and the crude product was purified by silica gel column chromatography (eluting with 1:30 EtOAc/77-heptane) affording the product 2,4-di-6>- ieri-butyldiphenylsilyl- 1 - -(4-chloro-3 -(4-ethoxybenzyl)phenyl)- β-D-glucopyranoside (0.30 g, 34%) as a white powder.
    1H NMR (400 MHz, CDC13) δ 7.56-7.54 (m, 2H), 7.43-7.31 (m, 13H), 7.29-7.22 (m, 6H), 7.07- 7.04 (m, 2H), 7.00 (d, J= 2.0 Hz, IH), 6.87 (dd, J= 8.4, 2.0 Hz, IH), 6.83-6.81 (m, 2H), 4.18 (d, J= 9.6 Hz, IH), 4.02 (q, J= 6.9 Hz, 2H), 3.96 (d, J= 10.8 Hz, 2H), 3.86 (ddd, J= 11.3, 7.7, 1.1 Hz, IH), 3.76 (ddd, J= 8.4, 8.4, 4.8 Hz, IH), 3.56 (ddd, J= 9.0, 6.4, 2.4 Hz, IH), 3.50 (dd, J=
    I I.4, 5.4 Hz, IH), 3.44 (dd, J= 9.4, 8.6 Hz, IH), 3.38 (dd, J= 8.8, 8.8 Hz, IH), 1.70 (dd, J= 7.8, 5.4 Hz, IH, OH), 1.42 (t, J= 6.8 Hz, 3H), 1.21 (d, J= 5.2 Hz, IH, OH), 1.00 (s, 9H), 0.64 (s, 9H); 13C NMR (100 MHz, CDC13) δ 157.4 (C), 138.8 (C), 137.4 (C), 136.3 (CH x2), 136.1 (CH x2), 135.2 (CH x2), 135.0 (C), 134.9 (CH x2), 134.8 (C), 134.2 (C), 132.8 (C), 132.0 (C), 131.6 (CH), 131.1 (C), 129.9 (CH x2), 129.7 (CH), 129.6 (CH), 129.5 (CH), 129.4 (CH), 129.2 (CH), 127.58 (CH x2), 127.57 (CH x2), 127.54 (CH x2), 127.31 (CH), 127.28 (CH x2), 114.4 (CH x2), 82.2 (CH), 80.5 (CH), 79.3 (CH), 76.3 (CH), 72.7 (CH), 63.4 (CH2), 62.7 (CH2), 38.2 (CH2), 27.2 (CH3 x3), 26.6 (CH3 x3), 19.6 (C), 19.2 (C), 14.9 (CH3). EXAMPLE 25 -Synthesis of dapagliflozin ((25,3R,4R,55,6/?)-2-[4-chloro-3-(4- ethoxybenzyl)phenyl]-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol; (Ij))

    IVj' U
    [0230] A solution of the 2,4-di-6>-ieri-butyldiphenylsilyl-l-C-(4-chloro-3-(4- ethoxybenzyl)phenyl)- -D-glucopyranoside (60 mg, 0.068 mmol) in THF (3.0 mL) and TBAF (3.0 mL, 3.0 mmol, 1.0 M in THF) was stirred at ambient temperature for 15 hours. CaC03 (0.62 g), Dowex^ 50WX8-400 ion exchange resin (1.86 g) and MeOH (5mL) were added to the product mixture and the suspension was stirred at ambient temperature for 1 hour and then the mixture was filtrated through a pad of diatomaceous earth. The filter cake was rinsed with MeOH and the combined filtrates was evaporated under vacuum and the resulting residue was purified by column chromatography (eluting with 1 : 10 MeOH/DCM) affording dapagliflozin (30 mg).

    1H NMR (400 MHz, CD3OD) δ 7.37-7.34 (m, 2H), 7.29 (dd, J= 8.2, 2.2 Hz, 1H), 7.12-7.10 (m, 2H), 6.82-6.80 (m, 2H), 4.10 (d, J= 9.6 Hz, 2H), 4.04 (d, J= 9.2 Hz, 2H), 4.00 (q, J= 7.1 Hz, 2H), 3.91-3.87 (m, 1H), 3.73-3.67(m, 1H), 3.47-3.40 (m, 3H), 3.31-3.23 (m, 2H), 1.37 (t, J= 7.0 Hz, 3H);  
    13C NMR (100 MHz, CD3OD) δ 157.4 (C), 138.6 (C), 138.5 (C), 133.1 (C), 131.5 (C), 130.5 (CH), 129.4 (CH x2), 128.7 (CH), 126.8 (CH), 114.0 (CH x2), 80.5 (CH), 80.8 (CH), 78.3 (CH), 75.0 (CH), 70.4 (CH), 63.0 (CH2), 61.7 (CH2), 37.8 (CH2), 13.8 (CH3); 

    LCMS (ESI) m/z 426 (100, [M+NH4]+), 428 (36, [M+NH4+2]+), 447 (33, [M+K]+). 

     Example 1 - Synthesis of l,6-anhydro-2,4-di-6>-ieri-butyldiphenylsilyl- -D-glucopyranose (II")

    III II"
    [0206] To a suspension solution of l,6-anhydro- -D-glucopyranose (1.83 g, 11.3 mmol) and imidazole (3.07 g, 45.2 mmol) in THF (10 mL) at 0 °C was added dropwise a solution of TBDPSC1 (11.6 mL, 45.2 mmol) in THF (10 mL). After the l,6-anhydro-P-D-gJucopyranose was consumed, water (10 mL) was added and the mixture was extracted twice with EtOAc (20 mL each), washed with brine (10 mL), dried (Na2S04) and concentrated. Column
    chromatography (eluting with 1 :20 EtOAc/rc-heptane) afforded 2,4-di-6>-ieri-butyldiphenylsilyl- l,6-anhydro- "D-glucopyranose (5.89 g, 81%).
    1H NMR (400 MHz, CDC13) δ 7.82-7.70 (m, 8H), 7.49-7.36 (m, 12H), 5.17 (s, IH), 4.22 (d, J= 4.8 Hz, IH), 3.88-3.85 (m, IH), 3.583-3.579 (m, IH), 3.492-3.486 (m, IH), 3.47-3.45 (m, IH), 3.30 (dd, J= 7.4, 5.4 Hz, IH), 1.71 (d, J= 6.0 Hz, IH), 1.142 (s, 9H), 1.139 (s, 9H); 13C NMR (100 MHz, CDCI3) δ 135.89 (CH x2), 135.87 (CH x2), 135.85 (CH x2), 135.83 (CH x2), 133.8 (C), 133.5 (C), 133.3 (C), 133.2 (C), 129.94 (CH), 129.92 (CH), 129.90 (CH), 129.88 (CH), 127.84 (CH2 x2), 127.82 (CH2 x2), 127.77 (CH2 x4), 102.4 (CH), 76.9 (CH), 75.3 (CH), 73.9 (CH), 73.5 (CH), 65.4 (CH2), 27.0 (CH3 x6), 19.3 (C x2).
    .........................
    Bristol-Myers Squibb and AstraZeneca type 2 diabetes drug dapagliflozin net Dag out chemical synthesis chemical synthesis of type 2 diabetes drug Farxiga_dapagliflozin_Forxiga from Bristol-Myers Sq