Sodium Azide → (Ethoxycarbonyloxy)ethyl (2R)-4-[(3-azidopropyl)sulfonyloxy]-3,3-dimethyl-2-(phenylmethoxy)butanoate

HRID 1919427Notes

Reaction equation

HRID 1919427 reaction equation
Cl[CH2:2][CH2:3][CH2:4][S:5]([O:8][CH2:9][C:10]([CH3:32])([CH3:31])[C@@H:11]([O:23][CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[C:12]([O:14][CH2:15][CH2:16][O:17][C:18]([O:20][CH2:21][CH3:22])=[O:19])=[O:13])(=[O:7])=[O:6].CC(C)([C@@H](OCC1C=CC=CC=1)C=C)CO.[N-:49]=[N+:50]=[N-:51].[Na+]>CS(C)=O>[N:49]([CH2:2][CH2:3][CH2:4][S:5]([O:8][CH2:9][C:10]([CH3:32])([CH3:31])[C@@H:11]([O:23][CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[C:12]([O:14][CH2:15][CH2:16][O:17][C:18]([O:20][CH2:21][CH3:22])=[O:19])=[O:13])(=[O:7])=[O:6])=[N+:50]=[N-:51]

Participants

5

Reactant 3

HCID 33557Sodium AzideHCID 10998568(3S)-2,2-Dimethyl-3-(phenylmethoxy)pent-4-en-1-olHCID 86628900(Ethoxycarbonyloxy)ethyl (2R)-4-[(3-chloropropyl)sulfonyloxy]-3,3-dimethyl-2-(phenylmethoxy)butanoate

Product 1

HCID 86628901(Ethoxycarbonyloxy)ethyl (2R)-4-[(3-azidopropyl)sulfonyloxy]-3,3-dimethyl-2-(phenylmethoxy)butanoate

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

Following the general procedure for the preparation of azides of Description 16, 11.0 g of a mixture of (ethoxycarbonyloxy)ethyl (2R)-4-[(3-chloropropyl)sulfonyloxy]-3,3-dimethyl-2-(phenylmethoxy)butanoate (32a) and (3R)-4,4-dimethyl-3-(phenylmethoxy)-3,4,5-trihydrofuran-2-one (1) dissolved in 100 mL of anhydrous dimethyl sulfoxide (DMSO) was reacted with 2.4 g (37 mmol) of sodium azide (NaN3). After work-up, the crude title compound (32b) was obtained and used in the next step without further purification. MS (ESI) m/z 524.07 (M+Na)+.

Sources & evidence

ORD record
ord-3ae1ebeb35974a5e9a32a1a70d9b92eb
Source dataset
uspto-grants-2012_05
Patent number
US08168617B2

Reaction notes

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