(2S,3S)-3-(ethoxycarbonyl)oxirane-2-carboxylic acid → Ethyl (2S,3S)-3-[[1-(S)-[alpha-(R)-hydroxybenzyl]-2-methyl-butyl]carbamoyl]oxirane-2-carboxylate

HRID 2120142Notes

Reaction equation

HRID 2120142 reaction equation
[CH2:1]([O:3][C:4]([C@H:6]1[O:8][C@@H:7]1[C:9]([OH:11])=O)=[O:5])[CH3:2].[NH2:12][C@@H:13]([CH:22]([CH3:25])[CH2:23][CH3:24])[C@@H:14]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[OH:15]>>[OH:15][C@@H:14]([C@@H:13]([NH:12][C:9]([C@H:7]1[O:8][C@@H:6]1[C:4]([O:3][CH2:1][CH3:2])=[O:5])=[O:11])[CH:22]([CH3:25])[CH2:23][CH3:24])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

3

Reactant 2

HCID 11030109(2S,3S)-3-(ethoxycarbonyl)oxirane-2-carboxylic acidHCID 12051470(1R,2S)-2-amino-3-methyl-1-phenyl-1-pentanol

Product 1

HCID 12051471Ethyl (2S,3S)-3-[[1-(S)-[alpha-(R)-hydroxybenzyl]-2-methyl-butyl]carbamoyl]oxirane-2-carboxylate

Procedure

The procedures of Example 1a were repeated employing (2S,3S)-3-ethoxycarbonyloxirane-2-carboxylic acid and (1R,2S)-2-amino-3-methyl-1-phenyl-1-pentanol (its preparation is described in the after-mentioned Reference Example 1), to prepare the titled compound.

Workup

  1. customits preparation

Sources & evidence

ORD record
ord-6ba1028c74bd4008bc8d1863f0dfb7d4
Source dataset
uspto-grants-2004_02
Patent number
US06689785B2

Reaction notes

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