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

HRID 2403188Notes

Reaction equation

HRID 2403188 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][C:22]([F:25])([F:24])[F:23])[CH2:11][NH:10]2)=[O:8])[CH2:5][CH2:4]1)#[N:2].[CH2:26]([O:28][C:29]([N:31]1[CH2:36][CH2:35][CH:34]([N:37]2[CH2:40][CH2:39][CH:38]2[C:41]([O-])=[O:42])[CH2:33][CH2:32]1)=[O:30])[CH3:27].[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][C:22]([F:25])([F:23])[F:24])[CH2:11][N:10]2[C:41]([CH:38]2[CH2:39][CH2:40][N:37]2[CH:34]2[CH2:33][CH2:32][N:31]([C:29]([O:28][CH2:26][CH3:27])=[O:30])[CH2:36][CH2:35]2)=[O:42])=[O:8])[CH2:4][CH2:5]1)#[N:2]

Participants

3

Reactant 2

HCID 86692747(2S,4R)-N-(1-cyanocyclopropyl)-4-(2-(trifluoromethoxy)phenylthio)pyrrolidine-2-carboxamideHCID 86692776Lithium 1-(1-(ethoxycarbonyl)piperidin-4-yl)azetidine-2-carboxylate

Product 1

HCID 71712112ethyl 4-(2-((2S,4R)-2-(1-cyanocyclopropylcarbamoyl)-4-(2-(trifluoromethoxy)phenylthio)pyrrolidine-1-carbonyl)azetidin-1-yl)piperidine-1-carboxylate

Procedure

The reaction of (2S,4R)-N-(1-cyanocyclopropyl)-4-(2-(trifluoromethoxy)phenylthio)pyrrolidine-2-carboxamide 12D 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-(trifluoromethoxy)phenylthio)pyrrolidine-1-carbonyl)azetidin-1-yl)piperidine-1-carboxylate 1:1 epimers as a white solid (70%). MS ISP (m/e): 610.3 (100) [(M+H)]+.

Sources & evidence

ORD record
ord-09a00dbd22114ac69f599b56d969124f
Source dataset
uspto-grants-2014_08
Patent number
US08802665B2

Reaction notes

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