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

HRID 1025338Notes

Reaction equation

HRID 1025338 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([C:11]([N:13]3[CH2:17][C@H:16]([S:18]([C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=4[Cl:27])(=[O:20])=[O:19])[CH2:15][C@H:14]3[C:28]([OH:30])=O)=[O:12])[CH2:10][CH2:9]2)=[CH:4][CH:3]=1.[NH2:31][C@@H:32]([CH2:41][CH2:42][CH3:43])[C@H:33]([OH:40])[C:34]([NH:36][CH:37]1[CH2:39][CH2:38]1)=[O:35]>>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([C:11]([N:13]3[CH2:17][C@H:16]([S:18]([C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=4[Cl:27])(=[O:19])=[O:20])[CH2:15][C@H:14]3[C:28]([NH:31][C@@H:32]([CH2:41][CH2:42][CH3:43])[C:33](=[O:40])[C:34]([NH:36][CH:37]3[CH2:39][CH2:38]3)=[O:35])=[O:30])=[O:12])[CH2:10][CH2:9]2)=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 16739337(2S,3S)-3-Amino-N-cyclopropyl-2-hydroxyhexanamideHCID 86762442(2S,4R)-1-[1-(4-bromo-phenyl)-cyclopropanecarbonyl]-4-(2-chloro-benzenesulfonyl)-pyrrolidine-2-carboxylic acid

Product 1

HCID 71577214(2S,4R)-1-(1-(4-bromophenyl)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,4R)-1-[1-(4-bromo-phenyl)-cyclopropanecarbonyl]-4-(2-chloro-benzenesulfonyl)-pyrrolidine-2-carboxylic acid and (2S,3S)-3-amino-N-cyclopropyl-2-hydroxyhexanamide in step 1. MS (m/e)=680.1 [M+H+].

Sources & evidence

ORD record
ord-452452457f784d5180ce2682d987cf12
Source dataset
uspto-grants-2014_05
Patent number
US08729061B2

Reaction notes

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