(2S,3S)-3-Amino-N-cyclopropyl-2-hydroxyhexanamide → (2S,4R)-1-(1-(5-chloro-3-fluoropyridin-2-yl)cyclopropanecarbonyl)-N-((S)-1-(cyclopropylamino)-1,2-dioxohexan-3-yl)-4-(2-(trifluoromethyl)phenylsulfonyl)pyrrolidine-2-carboxamide

HRID 1025340Notes

Reaction equation

HRID 1025340 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([F:34])[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[C:27]([F:30])([F:29])[F:28])(=[O:20])=[O:19])[CH2:15][C@H:14]3[C:31](O)=[O:32])=[O:12])[CH2:10][CH2:9]2)=[N:6][CH:7]=1.[NH2:35][C@@H:36]([CH2:45][CH2:46][CH3:47])[C@H:37]([OH:44])[C:38]([NH:40][CH:41]1[CH2:43][CH2:42]1)=[O:39]>>[Cl:1][C:2]1[CH:3]=[C:4]([F:34])[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[C:27]([F:30])([F:29])[F:28])(=[O:19])=[O:20])[CH2:15][C@H:14]3[C:31]([NH:35][C@@H:36]([CH2:45][CH2:46][CH3:47])[C:37](=[O:44])[C:38]([NH:40][CH:41]3[CH2:43][CH2:42]3)=[O:39])=[O:32])=[O:12])[CH2:10][CH2:9]2)=[N:6][CH:7]=1

Participants

3

Reactant 2

HCID 16739337(2S,3S)-3-Amino-N-cyclopropyl-2-hydroxyhexanamideHCID 86762443(2S,4R)-1-[1-(5-chloro-3-fluoro-pyridin-2-yl)-cyclopropanecarbonyl]-4-(2-trifluoromethyl-benzenesulfonyl)-pyrrolidine-2-carboxylic acid

Product 1

HCID 71577391(2S,4R)-1-(1-(5-chloro-3-fluoropyridin-2-yl)cyclopropanecarbonyl)-N-((S)-1-(cyclopropylamino)-1,2-dioxohexan-3-yl)-4-(2-(trifluoromethyl)phenylsulfonyl)pyrrolidine-2-carboxamide

Procedure

The title compound was prepared in analogy to Example 1, using (2S,4R)-1-[1-(5-chloro-3-fluoro-pyridin-2-yl)-cyclopropanecarbonyl]-4-(2-trifluoromethyl-benzenesulfonyl)-pyrrolidine-2-carboxylic acid and (2S,3S)-3-amino-N-cyclopropyl-2-hydroxyhexanamide in step 1. MS (m/e)=687.17 [M+H+].

Sources & evidence

ORD record
ord-e6fd4dc33ae34a99bd62ab23205ed637
Source dataset
uspto-grants-2014_05
Patent number
US08729061B2

Reaction notes

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