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

HRID 1025339Notes

Reaction equation

HRID 1025339 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]([I: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].[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]>>[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]([I:27])=[CH:23][CH:22]=3)[CH2:20][CH2:19]2)=[O:17])[C@H:13]([C:28]([NH:31][C@@H:32]([CH2:41][CH2:42][CH3:43])[C:33](=[O:40])[C:34]([NH:36][CH:37]2[CH2:39][CH2:38]2)=[O:35])=[O:30])[CH2:12]1)(=[O:9])=[O:10]

Participants

3

Reactant 2

HCID 16739337(2S,3S)-3-Amino-N-cyclopropyl-2-hydroxyhexanamideHCID 68502801(2S,4R)-4-(2-chloro-benzenesulfonyl)-1-[1-(4-iodo-phenyl)-cyclopropanecarbonyl]-pyrrolidine-2-carboxylic acid

Product 1

HCID 71577476(2S,4R)-4-(2-chlorophenylsulfonyl)-N-((S)-1-(cyclopropylamino)-1,2-dioxohexan-3-yl)-1-(1-(4-iodophenyl)cyclopropanecarbonyl)pyrrolidine-2-carboxamide

Procedure

The title compound was prepared in analogy to Example 1, using (2S,4R)-4-(2-chloro-benzenesulfonyl)-1-[1-(4-iodo-phenyl)-cyclopropanecarbonyl]-pyrrolidine-2-carboxylic acid and (2S,3S)-3-amino-N-cyclopropyl-2-hydroxyhexanamide in step 1. MS (m/e)=726.09 [M+H+].

Sources & evidence

ORD record
ord-d100cb7785b44aca9d13869dc2ea0d22
Source dataset
uspto-grants-2014_05
Patent number
US08729061B2

Reaction notes

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