(2S,4R)-4-(2-chloro-benzenesulfonyl)-1-[1-(5-chloro-3-fluoro-pyridin-2-yl)-cyclopropanecarbonyl]-pyrrolidine-2-carboxylic acid → (2S,4R)-1-(1-(5-chloro-3-fluoropyridin-2-yl)cyclopropanecarbonyl)-4-(2-chlorophenylsulfonyl)-N-((S)-1-(cyclopropylamino)-5-methyl-1,2-dioxohexan-3-yl)pyrrolidine-2-carboxamide

HRID 1025350Notes

Reaction equation

HRID 1025350 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8]([C@H:11]1[CH2:15][N:14]([C:16]([C:18]2([C:21]3[C:26]([F:27])=[CH:25][C:24]([Cl:28])=[CH:23][N:22]=3)[CH2:20][CH2:19]2)=[O:17])[C@H:13]([C:29]([OH:31])=O)[CH2:12]1)(=[O:10])=[O:9].[CH:32]1([NH:35][C:36](=[O:45])[C:37](=[O:44])[C@@H:38]([NH2:43])[CH2:39][CH:40]([CH3:42])[CH3:41])[CH2:34][CH2:33]1>>[Cl:28][C:24]1[CH:25]=[C:26]([F:27])[C:21]([C:18]2([C:16]([N:14]3[CH2:15][C@H:11]([S:8]([C:3]4[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=4[Cl:1])(=[O:9])=[O:10])[CH2:12][C@H:13]3[C:29]([NH:43][C@@H:38]([CH2:39][CH:40]([CH3:42])[CH3:41])[C:37](=[O:44])[C:36]([NH:35][CH:32]3[CH2:34][CH2:33]3)=[O:45])=[O:31])=[O:17])[CH2:19][CH2:20]2)=[N:22][CH:23]=1

Participants

3

Reactant 2

HCID 86762444(2S,4R)-4-(2-chloro-benzenesulfonyl)-1-[1-(5-chloro-3-fluoro-pyridin-2-yl)-cyclopropanecarbonyl]-pyrrolidine-2-carboxylic acidHCID 86762450(S)-3-Amino-5-methyl-2-oxo-hexanoic acid cyclopropylamide

Product 1

HCID 71577973(2S,4R)-1-(1-(5-chloro-3-fluoropyridin-2-yl)cyclopropanecarbonyl)-4-(2-chlorophenylsulfonyl)-N-((S)-1-(cyclopropylamino)-5-methyl-1,2-dioxohexan-3-yl)pyrrolidine-2-carboxamide

Procedure

The title compound was prepared in analogy to Example 1, using (2S,4R)-4-(2-Chloro-benzenesulfonyl)-1-[1-(5-chloro-3-fluoro-pyridin-2-yl)-cyclopropanecarbonyl]-pyrrolidine-2-carboxylic acid and (S)-3-Amino-5-methyl-2-oxo-hexanoic acid cyclopropylamide in step 1. MS (m/e)=667.15 [M+H+].

Sources & evidence

ORD record
ord-8ad65243411e430a806b25eb5acac0f8
Source dataset
uspto-grants-2014_05
Patent number
US08729061B2

Reaction notes

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