(2S,4R)-4-(2-chlorophenylsulfonyl)-N-(1-cyanocyclopropyl)pyrrolidine-2-carboxamide → HCID 71711170, compound

HRID 2403199Notes

Reaction equation

HRID 2403199 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][NH:14][C@H:13]([C:16]([NH:18][C:19]2([C:22]#[N:23])[CH2:21][CH2:20]2)=[O:17])[CH2:12]1)(=[O:10])=[O:9].[C:24]([O:28][C:29]([N:31]1[CH2:36][CH2:35][N:34]([C:37]2([C:40](O)=[O:41])[CH2:39][CH2:38]2)[CH2:33][CH2:32]1)=[O:30])([CH3:27])([CH3:26])[CH3:25]>>[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:40]([C:37]2([N:34]3[CH2:35][CH2:36][N:31]([C:29]([O:28][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:30])[CH2:32][CH2:33]3)[CH2:39][CH2:38]2)=[O:41])[C@H:13]([C:16](=[O:17])[NH:18][C:19]2([C:22]#[N:23])[CH2:21][CH2:20]2)[CH2:12]1)(=[O:10])=[O:9]

Participants

3

Reactant 2

HCID 46946413(2S,4R)-4-(2-chlorophenylsulfonyl)-N-(1-cyanocyclopropyl)pyrrolidine-2-carboxamideHCID 68761060HCID 68761060, compound

Product 1

HCID 71711170HCID 71711170, compoundYield 91%

Procedure

The reaction of (2S,4R)-4-(2-chlorophenylsulfonyl)-N-(1-cyanocyclopropyl)pyrrolidine-2-carboxamide 7H with 1-(4-(tert-butoxycarbonyl)piperazin-1-yl)cyclopropanecarboxylic acid 16E carried out according to the general procedure L yielded tert-butyl 4-(1-((2S,4R)-4-(2-chlorophenylsulfonyl)-2-(1-cyanocyclopropylcarbamoyl)pyrrolidine-1-carbonyl)cyclopropyl)piperazine-1-carboxylate as a white solid (91%). MS ISN (m/e): 604.4/606.3 (41/15) [(M−H)]−, 664.3/666.4 (100/54) [(M+OAc)]−.

Sources & evidence

ORD record
ord-81f2d99bca6a438fa99c761e5d85f924
Source dataset
uspto-grants-2014_08
Patent number
US08802665B2

Reaction notes

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