(2S,4R)-N-(1-cyanocyclopropyl)-4-(2-methoxyphenylthio)pyrrolidine-2-carboxamide → ethyl 4-(2-((2S,4R)-2-(1-cyanocyclopropylcarbamoyl)-4-(2-methoxyphenylthio)pyrrolidine-1-carbonyl)azetidin-1-yl)piperidine-1-carboxylate

HRID 2403187Notes

Reaction equation

HRID 2403187 reaction equation
[C:1]([C:3]1([NH:6][C:7]([C@@H:9]2[CH2:13][C@@H:12]([S:14][C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=3[O:21][CH3:22])[CH2:11][NH:10]2)=[O:8])[CH2:5][CH2:4]1)#[N:2].[CH2:23]([O:25][C:26]([N:28]1[CH2:33][CH2:32][CH:31]([N:34]2[CH2:37][CH2:36][CH:35]2[C:38]([O-])=[O:39])[CH2:30][CH2:29]1)=[O:27])[CH3:24].[Li+]>>[C:1]([C:3]1([NH:6][C:7]([C@@H:9]2[CH2:13][C@@H:12]([S:14][C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=3[O:21][CH3:22])[CH2:11][N:10]2[C:38]([CH:35]2[CH2:36][CH2:37][N:34]2[CH:31]2[CH2:30][CH2:29][N:28]([C:26]([O:25][CH2:23][CH3:24])=[O:27])[CH2:33][CH2:32]2)=[O:39])=[O:8])[CH2:5][CH2:4]1)#[N:2]

Participants

3

Reactant 2

HCID 86692745(2S,4R)-N-(1-cyanocyclopropyl)-4-(2-methoxyphenylthio)pyrrolidine-2-carboxamideHCID 86692776Lithium 1-(1-(ethoxycarbonyl)piperidin-4-yl)azetidine-2-carboxylate

Product 1

HCID 71712111ethyl 4-(2-((2S,4R)-2-(1-cyanocyclopropylcarbamoyl)-4-(2-methoxyphenylthio)pyrrolidine-1-carbonyl)azetidin-1-yl)piperidine-1-carboxylate

Procedure

The reaction of (2S,4R)-N-(1-cyanocyclopropyl)-4-(2-methoxyphenylthio)pyrrolidine-2-carboxamide 12C 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)-2-(1-cyanocyclopropylcarbamoyl)-4-(2-methoxyphenylthio)pyrrolidine-1-carbonyl)azetidin-1-yl)piperidine-1-carboxylate 1:1 epimers as a white solid (67%). MS ISP (m/e): 556.2 (100) [(M+H)]+.

Sources & evidence

ORD record
ord-6991c3beb04346af8095222231a5e8c6
Source dataset
uspto-grants-2014_08
Patent number
US08802665B2

Reaction notes

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