Ethyl 3-Hydroxybutyrate → ethyl (S)-4-azido-3-hydroxybutyrate

HRID 1723612Notes

Reaction equation

HRID 1723612 reaction equation
OC(C)CC(OCC)=O.[N:10]([CH2:13][CH:14]([OH:21])[CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17])=[N+:11]=[N-:12]>>[N:10]([CH2:13][C@@H:14]([OH:21])[CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17])=[N+:11]=[N-:12]

Participants

3

Reactant 2

HCID 62572Ethyl 3-HydroxybutyrateHCID 14685344Ethyl 4-azido-3-hydroxybutyrate

Product 1

HCID 10888398ethyl (S)-4-azido-3-hydroxybutyrateYield 80.2%

Procedure

Instead of ethyl 3-hydroxybutyrate used in Example 1, ethyl 4-azido-3-hydroxybutyrate was used. The reaction was carried out for 1 hour and ethyl (S)-4-azido-3-hydroxybutyrate (80.2% e.e) was obtained at 83.5% conversion.

Sources & evidence

ORD record
ord-db7f65637b054d018429f55febfd6198
Source dataset
uspto-grants-2009_02
Patent number
US07485452B2

Reaction notes

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