Lithium 1-(1-(ethoxycarbonyl)piperidin-4-yl)azetidine-2-carboxylate → ethyl 4-(2-((2S,4R)-2-(1-cyanocyclopropylcarbamoyl)-4-(3-(trifluoromethyl)phenylsulfonyl)pyrrolidine-1-carbonyl)azetidin-1-yl)piperidine-1-carboxylate
Reaction equation
[C:1]([C:3]1([NH:6][C:7]([C@@H:9]2[CH2:13][C@@H:12]([S:14]([C:17]3[CH:22]=[CH:21][CH:20]=[C:19]([C:23]([F:26])([F:25])[F:24])[CH:18]=3)(=[O:16])=[O:15])[CH2:11][NH:10]2)=[O:8])[CH2:5][CH2:4]1)#[N:2].[CH2:27]([O:29][C:30]([N:32]1[CH2:37][CH2:36][CH:35]([N:38]2[CH2:41][CH2:40][CH:39]2[C:42]([O-])=[O:43])[CH2:34][CH2:33]1)=[O:31])[CH3:28].[Li+]>>[C:1]([C:3]1([NH:6][C:7]([C@@H:9]2[CH2:13][C@@H:12]([S:14]([C:17]3[CH:22]=[CH:21][CH:20]=[C:19]([C:23]([F:26])([F:24])[F:25])[CH:18]=3)(=[O:16])=[O:15])[CH2:11][N:10]2[C:42]([CH:39]2[CH2:40][CH2:41][N:38]2[CH:35]2[CH2:34][CH2:33][N:32]([C:30]([O:29][CH2:27][CH3:28])=[O:31])[CH2:37][CH2:36]2)=[O:43])=[O:8])[CH2:4][CH2:5]1)#[N:2]Participants
3
Reactant 2
Product 1
Procedure
The reaction of (2S,4R)-N-(1-cyanocyclopropyl)-4-(3-(trifluoromethyl)phenylsulfonyl)pyrrolidine-2-carboxamide 7E 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)phenylsulfonyl)pyrrolidine-1-carbonyl)azetidin-1-yl)piperidine-1-carboxylate 1:1 epimers as a white solid (77%). MS ISP (m/e): 626.3 (100) [(M+H)]+.
Sources & evidence
- ORD record
- ord-49cc396b0d834fc99f6bb5e744b6fddb
- Source dataset
- uspto-grants-2014_08
- Patent number
- US08802665B2
Reaction notes
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