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

HRID 1671457Notes

Reaction equation

HRID 1671457 reaction equation
Cl[CH2:2][CH2:3][CH2:4][S:5]([O:8][CH2:9][C:10]([CH3:30])([CH3:29])[C@@H:11]([O:21][CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[C:12]([O:14][CH2:15][C:16](=[O:20])[N:17]([CH3:19])[CH3:18])=[O:13])(=[O:7])=[O:6].[N-:31]=[N+:32]=[N-:33].[Na+]>CS(C)=O>[N:31]([CH2:2][CH2:3][CH2:4][S:5]([O:8][CH2:9][C:10]([CH3:30])([CH3:29])[C@@H:11]([O:21][CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[C:12]([O:14][CH2:15][C:16](=[O:20])[N:17]([CH3:19])[CH3:18])=[O:13])(=[O:7])=[O:6])=[N+:32]=[N-:33]

Participants

4

Reactant 2

HCID 33557Sodium AzideHCID 86629049(N,N-Dimethylcarbamoyl)methyl (2R)-4-[(3-chloropropyl)sulfonyloxy]-3,3-dimethyl-2-(phenylmethoxy)butanoate

Product 1

HCID 86629050(N,N-Dimethylcarbamoyl)methyl (2R)-4-[(3-azidopropyl)sulfonyloxy]-3,3-dimethyl-2-(phenylmethoxy)butanoateYield 91%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

Following the general procedure for the preparation of azides of Description 16, (N,N-dimethylcarbamoyl)methyl (2R)-4-[(3-chloropropyl)sulfonyloxy]-3,3-dimethyl-2-(phenylmethoxy)butanoate (36c) (200 mg, 0.43 mmol) dissolved in 3 mL of anhydrous dimethyl sulfoxide (DMSO) was reacted with 130 mg (2.0 mmol) of sodium azide (NaN3). After work-up, the crude material (36d) 184 mg (91% yield) was obtained as a colorless viscous oil that was used in the next step without further purification. MS (ESI) m/z 471.2 (M+H)+, 493.1 (M+Na)+.

Sources & evidence

ORD record
ord-85c664d4b41940bbae72ca900d3ffbdc
Source dataset
uspto-grants-2011_08
Patent number
US07994218B2

Reaction notes

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