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

HRID 2403178Notes

Reaction equation

HRID 2403178 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].[F:24][C:25]([F:41])([F:40])[CH2:26][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.[Li+]>>[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:37]([CH:34]2[CH2:35][CH2:36][N:33]2[CH:30]2[CH2:29][CH2:28][N:27]([CH2:26][C:25]([F:40])([F:24])[F:41])[CH2:32][CH2:31]2)=[O:38])[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]

Participants

3

Reactant 2

HCID 46946413(2S,4R)-4-(2-chlorophenylsulfonyl)-N-(1-cyanocyclopropyl)pyrrolidine-2-carboxamideHCID 86692769Lithium 1-(1-(2,2,2-trifluoroethyl)piperidin-4-yl)azetidine-2-carboxylate

Product 1

HCID 71711973(2S,4R)-4-(2-chlorophenylsulfonyl)-N-(1-cyanocyclopropyl)-1-(1-(1-(2,2,2-trifluoroethyl)piperidin-4-yl)azetidine-2-carbonyl)pyrrolidine-2-carboxamide

Procedure

The reaction of (2S,4R)-4-(2-chlorophenylsulfonyl)-N-(1-cyanocyclopropyl)pyrrolidine-2-carboxamide 7H and lithium 1-(1-(2,2,2-trifluoroethyl)piperidin-4-yl)azetidine-2-carboxylate 20G carried out according to the general procedure L yielded (2S,4R)-4-(2-chlorophenylsulfonyl)-N-(1-cyanocyclopropyl)-1-(1-(1-(2,2,2-trifluoroethyl)piperidin-4-yl)azetidine-2-carbonyl)pyrrolidine-2-carboxamide 1:1 epimers as an off-white solid (65%). MS ISP (m/e): 602.3 (100) [(M+H)]]+.

Sources & evidence

ORD record
ord-2d267320b4554f7fb4f5db7d2638a5e0
Source dataset
uspto-grants-2014_08
Patent number
US08802665B2

Reaction notes

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