(2S,4R)-4-(2-chlorophenylsulfonyl)-N-(1-cyanocyclopropyl)pyrrolidine-2-carboxamide → (2S,4R)-1-(1-(1-acetylpiperidin-4-yl)azetidine-2-carbonyl)-4-(2-chlorophenylsulfonyl)-N-(1-cyanocyclopropyl)pyrrolidine-2-carboxamide

HRID 2403177Notes

Reaction equation

HRID 2403177 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]([N:27]1[CH2:32][CH2:31][CH:30]([N:33]2[CH2:36][CH2:35][CH:34]2[C:37]([O-])=[O:38])[CH2:29][CH2:28]1)(=[O:26])[CH3:25].[Li+]>>[C:24]([N:27]1[CH2:28][CH2:29][CH:30]([N:33]2[CH2:36][CH2:35][CH:34]2[C:37]([N:14]2[CH2:15][C@H:11]([S:8]([C:3]3[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=3[Cl:1])(=[O:10])=[O:9])[CH2:12][C@H:13]2[C:16]([NH:18][C:19]2([C:22]#[N:23])[CH2:21][CH2:20]2)=[O:17])=[O:38])[CH2:31][CH2:32]1)(=[O:26])[CH3:25]

Participants

3

Reactant 2

HCID 46946413(2S,4R)-4-(2-chlorophenylsulfonyl)-N-(1-cyanocyclopropyl)pyrrolidine-2-carboxamideHCID 86692767Lithium 1-(1-acetylpiperidin-4-yl)azetidine-2-carboxylate

Product 1

HCID 71711972(2S,4R)-1-(1-(1-acetylpiperidin-4-yl)azetidine-2-carbonyl)-4-(2-chlorophenylsulfonyl)-N-(1-cyanocyclopropyl)pyrrolidine-2-carboxamide

Procedure

The reaction of (2S,4R)-4-(2-chlorophenylsulfonyl)-N-(1-cyanocyclopropyl)pyrrolidine-2-carboxamide 7H and lithium 1-(1-acetylpiperidin-4-yl)azetidine-2-carboxylate 20F carried out according to the general procedure L yielded (2S,4R)-1-(1-(1-acetylpiperidin-4-yl)azetidine-2-carbonyl)-4-(2-chlorophenylsulfonyl)-N-(1-cyanocyclopropyl)pyrrolidine-2-carboxamide 1:1 epimers as an off-white solid (93%). MS ISP (m/e): 526.3 (100) [(M+H)]]+.

Sources & evidence

ORD record
ord-b1edbb1baf4846d8a83334b2fdc76e26
Source dataset
uspto-grants-2014_08
Patent number
US08802665B2

Reaction notes

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