(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-(butylamino)-1,2-dioxohexan-3-yl)-1-(1-(5-chloro-3-fluoropyridin-2-yl)cyclopropanecarbonyl)-4-(2-chlorophenylsulfonyl)pyrrolidine-2-carboxamide

HRID 1025352Notes

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:36][C:37](=[O:45])[C:38](=[O:44])[C@@H:39]([NH2:43])[CH2:40][CH2:41][CH3:42])[CH2:33][CH2:34][CH3:35]>>[CH2:32]([NH:36][C:37](=[O:45])[C:38](=[O:44])[C@@H:39]([NH:43][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:9])=[O:10])[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)[CH2:20][CH2:19]1)=[O:17])=[O:30])[CH2:40][CH2:41][CH3:42])[CH2:33][CH2:34][CH3:35]

Participants

Reactant 2

HCID 86762444(2S,4R)-4-(2-chloro-benzenesulfonyl)-1-[1-(5-chloro-3-fluoro-pyridin-2-yl)-cyclopropanecarbonyl]-pyrrolidine-2-carboxylic acid

HCID 86762452(S)-3-Amino-2-oxo-hexanoic acid butylamide

Product 1

HCID 71577897(2S,4R)-N-((S)-1-(butylamino)-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 butylamide in step 1. MS (m/e)=669.17 [M+H+].

Sources & evidence

ORD record: ord-9d6b196210bf45008a008528f4d7fab4
Source dataset: uspto-grants-2014_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08729061B2

Reaction notes

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