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

HRID 2403172Notes

Reaction equation

HRID 2403172 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].[CH:24]1([N:30]2[CH2:33][CH2:32][CH:31]2[C:34]([O-])=[O:35])[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]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:34]([CH:31]2[CH2:32][CH2:33][N:30]2[CH:24]2[CH2:25][CH2:26][CH2:27][CH2:28][CH2:29]2)=[O:35])[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 86692757Lithium 1-cyclohexylazetidine-2-carboxylate

Product 1

HCID 71711902(2S,4R)-4-(2-chlorophenylsulfonyl)-N-(1-cyanocyclopropyl)-1-(1-cyclohexylazetidine-2-carbonyl)pyrrolidine-2-carboxamide

Procedure

The reaction of (2S,4R)-4-(2-chlorophenylsulfonyl)-N-(1-cyanocyclopropyl)pyrrolidine-2-carboxamide 7H and lithium 1-cyclohexylazetidine-2-carboxylate 20A carried out according to the general procedure L yielded (2S,4R)-4-(2-chlorophenylsulfonyl)-N-(1-cyanocyclopropyl)-1-(1-cyclohexylazetidine-2-carbonyl)pyrrolidine-2-carboxamide 1:1 epimers as an off-white solid (69%). MS ISP (m/e): 519.2 (100) [(M+H)]]+.

Sources & evidence

ORD record
ord-5f431a9f56b8402ab9ff177cfa62f3c5
Source dataset
uspto-grants-2014_08
Patent number
US08802665B2

Reaction notes

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