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

HRID 1025353Notes

Reaction equation

HRID 1025353 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](O)=[O:30])[CH2:12]1)(=[O:10])=[O:9].[CH2:32]([NH:39][C:40](=[O:48])[C:41](=[O:47])[C@@H:42]([NH2:46])[CH2:43][CH2:44][CH3:45])[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1>>[CH2:32]([NH:39][C:40](=[O:48])[C:41](=[O:47])[C@@H:42]([NH:46][C:29]([C@@H:13]1[CH2:12][C@@H:11]([S:8]([C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=2[Cl:1])(=[O:10])=[O:9])[CH2:15][N:14]1[C:16]([C:18]1([C:21]2[C:26]([F:27])=[CH:25][C:24]([Cl:28])=[CH:23][N:22]=2)[CH2:19][CH2:20]1)=[O:17])=[O:30])[CH2:43][CH2:44][CH3:45])[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=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 86762453(S)-3-Amino-2-oxo-hexanoic acid benzylamide

Product 1

HCID 71577896(2S,4R)-N-((S)-1-(benzylamino)-1,2-dioxohexan-3-yl)-1-(1-(5-chloro-3-fluoropyridin-2-yl)cyclopropanecarbonyl)-4-(2-chlorophenylsulfonyl)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-2-oxo-hexanoic acid benzylamide in step 1. MS (m/e)=703.15 [M+H+].

Sources & evidence

ORD record
ord-238f67835b8e45cd83a8982417263f4b
Source dataset
uspto-grants-2014_05
Patent number
US08729061B2

Reaction notes

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