(2S,4R)-1-(1-(4-chlorophenyl)cyclopropanecarbonyl)-4-(2-chlorophenylsulfonyl)pyrrolidine-2-carboxylic acid → (2S,4R)-1-(1-(4-chlorophenyl)cyclopropanecarbonyl)-4-(2-chlorophenylsulfonyl)-N-((S)-1-(isobutylamino)-1,2-dioxopentan-3-yl)pyrrolidine-2-carboxamide

HRID 1025346Notes

Reaction equation

HRID 1025346 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[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][CH:22]=3)[CH2:20][CH2:19]2)=[O:17])[C@H:13]([C:28]([OH:30])=O)[CH2:12]1)(=[O:10])=[O:9].[CH2:31]([NH:35][C:36](=[O:43])[C:37](=[O:42])[C@@H:38]([NH2:41])[CH2:39][CH3:40])[CH:32]([CH3:34])[CH3:33]>>[Cl:27][C:24]1[CH:25]=[CH:26][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:10])=[O:9])[CH2:12][C@H:13]3[C:28]([NH:41][C@@H:38]([CH2:39][CH3:40])[C:37](=[O:42])[C:36]([NH:35][CH2:31][CH:32]([CH3:33])[CH3:34])=[O:43])=[O:30])=[O:17])[CH2:20][CH2:19]2)=[CH:22][CH:23]=1

Participants

3

Reactant 2

HCID 68503876(2S,4R)-1-(1-(4-chlorophenyl)cyclopropanecarbonyl)-4-(2-chlorophenylsulfonyl)pyrrolidine-2-carboxylic acidHCID 86762446(S)-3-Amino-2-oxo-pentanoic acid isobutyl-amide

Product 1

HCID 71578054(2S,4R)-1-(1-(4-chlorophenyl)cyclopropanecarbonyl)-4-(2-chlorophenylsulfonyl)-N-((S)-1-(isobutylamino)-1,2-dioxopentan-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-(4-chloro-phenyl)-cyclopropanecarbonyl]-pyrrolidine-2-carboxylic acid and (S)-3-Amino-2-oxo-pentanoic acid isobutyl-amide in step 1. MS (m/e)=636.17 [M+H+].

Sources & evidence

ORD record
ord-4bf5b32ec46943fd9d149eb9e951b0ee
Source dataset
uspto-grants-2014_05
Patent number
US08729061B2

Reaction notes

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