Lithium 1-(1-(ethoxycarbonyl)piperidin-4-yl)azetidine-2-carboxylate → ethyl 4-(2-((2S,4R)-2-(1-cyanocyclopropylcarbamoyl)-4-(3-(trifluoromethyl)phenylthio)pyrrolidine-1-carbonyl)azetidin-1-yl)piperidine-1-carboxylate

HRID 2403189Notes

Reaction equation

HRID 2403189 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]=[C:17]([C:21]([F:24])([F:23])[F:22])[CH:16]=3)[CH2:11][NH:10]2)=[O:8])[CH2:5][CH2:4]1)#[N:2].[CH2:25]([O:27][C:28]([N:30]1[CH2:35][CH2:34][CH:33]([N:36]2[CH2:39][CH2:38][CH:37]2[C:40]([O-])=[O:41])[CH2:32][CH2:31]1)=[O:29])[CH3:26].[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]=[C:17]([C:21]([F:24])([F:22])[F:23])[CH:16]=3)[CH2:11][N:10]2[C:40]([CH:37]2[CH2:38][CH2:39][N:36]2[CH:33]2[CH2:32][CH2:31][N:30]([C:28]([O:27][CH2:25][CH3:26])=[O:29])[CH2:35][CH2:34]2)=[O:41])=[O:8])[CH2:4][CH2:5]1)#[N:2]

Participants

3

Reactant 2

HCID 86692776Lithium 1-(1-(ethoxycarbonyl)piperidin-4-yl)azetidine-2-carboxylateHCID 86692781(2S,4R)-N-(1-cyanocyclopropyl)-4-(3-(trifluoromethyl)phenylthio)pyrrolidine-2-carboxamide

Product 1

HCID 71712113ethyl 4-(2-((2S,4R)-2-(1-cyanocyclopropylcarbamoyl)-4-(3-(trifluoromethyl)phenylthio)pyrrolidine-1-carbonyl)azetidin-1-yl)piperidine-1-carboxylate

Procedure

The reaction of (2S,4R)-N-(1-cyanocyclopropyl)-4-(3-(trifluoromethyl)phenylthio)pyrrolidine-2-carboxamide 12E 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-(3-(trifluoromethyl)phenylthio)pyrrolidine-1-carbonyl)azetidin-1-yl)piperidine-1-carboxylate 1:1 epimers as a white solid (58%). MS ISP (m/e): 594.4 (100) [(M+H)]+.

Sources & evidence

ORD record
ord-18800e0e78954641957fac5871f0526a
Source dataset
uspto-grants-2014_08
Patent number
US08802665B2

Reaction notes

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