Lithium 1-(1-(ethoxycarbonyl)piperidin-4-yl)azetidine-2-carboxylate → ethyl 4-(2-((2S,4R)-4-(4-chlorophenylthio)-2-(1-cyanocyclopropylcarbamoyl)pyrrolidine-1-carbonyl)azetidin-1-yl)piperidine-1-carboxylate

HRID 2403186Notes

Reaction equation

HRID 2403186 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][C@H:9]2[CH2:13][NH:12][C@H:11]([C:14]([NH:16][C:17]3([C:20]#[N:21])[CH2:19][CH2:18]3)=[O:15])[CH2:10]2)=[CH:4][CH:3]=1.[CH2:22]([O:24][C:25]([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])[CH3:23].[Li+]>>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][C@H:9]2[CH2:13][N:12]([C:37]([CH:34]3[CH2:35][CH2:36][N:33]3[CH:30]3[CH2:29][CH2:28][N:27]([C:25]([O:24][CH2:22][CH3:23])=[O:26])[CH2:32][CH2:31]3)=[O:38])[C@H:11]([C:14](=[O:15])[NH:16][C:17]3([C:20]#[N:21])[CH2:19][CH2:18]3)[CH2:10]2)=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 86692776Lithium 1-(1-(ethoxycarbonyl)piperidin-4-yl)azetidine-2-carboxylateHCID 86692780(2S,4R)-4-(4-chlorophenylthio)-N-(1-cyanocyclopropyl)pyrrolidine-2-carboxamide

Product 1

HCID 71712044ethyl 4-(2-((2S,4R)-4-(4-chlorophenylthio)-2-(1-cyanocyclopropylcarbamoyl)pyrrolidine-1-carbonyl)azetidin-1-yl)piperidine-1-carboxylate

Procedure

The reaction of (2S,4R)-4-(4-chlorophenylthio)-N-(1-cyanocyclopropyl)pyrrolidine-2-carboxamide 12G and lithium 1-(1-(ethoxycarbonyl)piperidin-4-yl)azetidine-2-carboxylate 20J carried out according to the general procedure L yielded ethyl 4-(2-((2S,4R)-4-(4-chlorophenylthio)-2-(1-cyanocyclopropylcarbamoyl)pyrrolidine-1-carbonyl)azetidin-1-yl)piperidine-1-carboxylate 1:1 epimers as a white solid (70%). MS ISP (m/e): 560.3/562.1 (100/62) [(M+H)]+.

Sources & evidence

ORD record
ord-6ccb0065273b4e308f8ae83a90645bf6
Source dataset
uspto-grants-2014_08
Patent number
US08802665B2

Reaction notes

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