(2S,3S)-3-Amino-N-cyclopropyl-2-hydroxyhexanamide → (2S,4R)-1-(1-(4-chlorophenyl)cyclopropanecarbonyl)-4-(2-chlorophenylsulfonyl)-N-((S)-1-(cyclopropylamino)-1,2-dioxohexan-3-yl)pyrrolidine-2-carboxamide

HRID 1025337Notes

Reaction equation

HRID 1025337 reaction equation
[NH2:1][C@@H:2]([CH2:11][CH2:12][CH3:13])[C@H:3]([OH:10])[C:4]([NH:6][CH:7]1[CH2:9][CH2:8]1)=[O:5].[Cl:14][C:15]1[CH:20]=[CH:19][C:18]([C:21]2([C:24]([N:26]3[CH2:30][C@H:29]([S:31]([C:34]4[CH:39]=[CH:38][CH:37]=[CH:36][C:35]=4[Cl:40])(=[O:33])=[O:32])[CH2:28][C@H:27]3[C:41](O)=[O:42])=[O:25])[CH2:23][CH2:22]2)=[CH:17][CH:16]=1>>[Cl:14][C:15]1[CH:20]=[CH:19][C:18]([C:21]2([C:24]([N:26]3[CH2:30][C@H:29]([S:31]([C:34]4[CH:39]=[CH:38][CH:37]=[CH:36][C:35]=4[Cl:40])(=[O:32])=[O:33])[CH2:28][C@H:27]3[C:41]([NH:1][C@@H:2]([CH2:11][CH2:12][CH3:13])[C:3](=[O:10])[C:4]([NH:6][CH:7]3[CH2:8][CH2:9]3)=[O:5])=[O:42])=[O:25])[CH2:23][CH2:22]2)=[CH:17][CH:16]=1

Participants

3

Reactant 2

HCID 16739337(2S,3S)-3-Amino-N-cyclopropyl-2-hydroxyhexanamideHCID 68503876(2S,4R)-1-(1-(4-chlorophenyl)cyclopropanecarbonyl)-4-(2-chlorophenylsulfonyl)pyrrolidine-2-carboxylic acid

Product 1

HCID 71577128(2S,4R)-1-(1-(4-chlorophenyl)cyclopropanecarbonyl)-4-(2-chlorophenylsulfonyl)-N-((S)-1-(cyclopropylamino)-1,2-dioxohexan-3-yl)pyrrolidine-2-carboxamide

Procedure

The title compound was prepared in analogy to Example 1, using (2S,3S)-3-amino-N-cyclopropyl-2-hydroxyhexanamide and (2S,4R)-1-(1-(4-chlorophenyl)cyclopropanecarbonyl)-4-(2-chlorophenylsulfonyl)pyrrolidine-2-carboxylic acid in step 1. MS (m/e)=634.15 [M+H+].

Sources & evidence

ORD record
ord-06805525dcd54aeca04d87c708f4f5bd
Source dataset
uspto-grants-2014_05
Patent number
US08729061B2

Reaction notes

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