Sodium Azide → HCID 86628909, compound

HRID 1919440Notes

Reaction equation

HRID 1919440 reaction equation
Cl[CH2:2][CH2:3][CH2:4][S:5]([O:8][CH2:9][C:10]([CH3:33])([CH3:32])[C@@H:11]([O:24][CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[C:12]([O:14][CH2:15][CH2:16][O:17][C:18]([O:20][CH:21]([CH3:23])[CH3:22])=[O:19])=[O:13])(=[O:7])=[O:6].[N-:34]=[N+:35]=[N-:36].[Na+]>CS(C)=O>[N:34]([CH2:2][CH2:3][CH2:4][S:5]([O:8][CH2:9][C:10]([CH3:33])([CH3:32])[C@@H:11]([O:24][CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[C:12]([O:14][CH2:15][CH2:16][O:17][C:18]([O:20][CH:21]([CH3:23])[CH3:22])=[O:19])=[O:13])(=[O:7])=[O:6])=[N+:35]=[N-:36]

Participants

4

Reactant 2

HCID 33557Sodium AzideHCID 86628908HCID 86628908, compound

Product 1

HCID 86628909HCID 86628909, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

Following the general procedure for the preparation of azides of Description 16, 23.0 g (45.3 mmol) of (methylethoxycarbonyloxy)ethyl (2R)-4-[(3-chloropropyl)sulfonyloxy]-3,3-dimethyl-2-(phenylmethoxy)butanoate (40a) dissolved in 210 mL of anhydrous dimethyl sulfoxide (DMSO) was reacted with 5.9 g (93.6 mmol) of sodium azide (NaN3). After work-up, the crude title compound (40b) was obtained and used in the next step without further purification. Rf=0.29 (EtOAc/Hxn=1:4). 1H NMR (400 MHz, CDCl3, both diastereomers): δ=1.06-1.08 (m, 6H), 1.24-1.35 (m, 6H), 1.57 (d, J=5.2 Hz, 3H), 2.03-2.10 (m, 2H), 3.10-3.16 (m, 2H), 3.44-3.48 (m, 2H), 3.84-3.85 (2s, 1H), 3.94-3.96 (2d, J=8.8, 9.2 Hz, 1H), 4.18-4.22 (2d, J=9.2, 9.6 Hz, 1H), 4.33-4.38 (2d, J=11.2, 11.2 Hz, 1H), 4.64 (t, J=11.2 Hz, 1H), 4.78-4.97 (m, 1H), 6.82-6.87 (m, 1H), 7.32-7.37 (m, 5H) ppm. MS (ESI) m/z 538.07 (M+Na)+. The analytical data was consistent with the proposed structure.

Sources & evidence

ORD record
ord-d4abcc5ec93748eea523578cf319eb33
Source dataset
uspto-grants-2012_05
Patent number
US08168617B2

Reaction notes

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