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

HRID 1919421Notes

Reaction equation

HRID 1919421 reaction equation
Cl[CH2:2][CH2:3][CH2:4][S:5]([O:8][CH2:9][C:10]([CH3:35])([CH3:34])[C@@H:11]([O:26][CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)[C:12]([O:14][CH2:15][O:16][C:17](=[O:25])[CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)=[O:13])(=[O:7])=[O:6].[N-:36]=[N+:37]=[N-:38].[Na+]>CS(C)=O>[N:36]([CH2:2][CH2:3][CH2:4][S:5]([O:8][CH2:9][C:10]([CH3:35])([CH3:34])[C@@H:11]([O:26][CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)[C:12]([O:14][CH2:15][O:16][C:17](=[O:25])[CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)=[O:13])(=[O:7])=[O:6])=[N+:37]=[N-:38]

Participants

4

Reactant 2

HCID 33557Sodium AzideHCID 86628893(2-Phenylacetyloxy)methyl (2R)-4-[(3-chloropropyl)sulfonyloxy]-3,3-dimethyl-2-(phenylmethoxy)butanoate

Product 1

HCID 86628894(2-Phenylacetyloxy)methyl (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, (2-phenylacetyloxy)methyl (2R)-4-[(3-chloropropyl)sulfonyloxy]-3,3-dimethyl-2-(phenylmethoxy)butanoate (28a) (0.44 g, 0.84 mmol) dissolved in 5 mL of anhydrous dimethyl sulfoxide (DMSO) was reacted with 140 mg (2.1 mmol) of sodium azide (NaN3). After work-up, the crude title compound (28b) was used in the next step without further purification. MS (ESI) m/z 556.12 (M+Na)+.

Workup

  1. customAfter work-up, the crude title compound (28b) was used in the next step without further purification

Sources & evidence

ORD record
ord-1ccdeb7ffe0e4d81a93d2e2b5f4d3314
Source dataset
uspto-grants-2012_05
Patent number
US08168617B2

Reaction notes

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