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

HRID 2403191Notes

Reaction equation

HRID 2403191 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:23]=[CH:22][C:20]([CH3:21])=[CH:19][CH:18]=3)(=[O:16])=[O:15])[CH2:11][NH:10]2)=[O:8])[CH2:5][CH2:4]1)#[N:2].[CH2:24]([O:26][C:27]([N:29]1[CH2:34][CH2:33][CH:32]([N:35]2[CH2:38][CH2:37][CH:36]2[C:39]([O-])=[O:40])[CH2:31][CH2:30]1)=[O:28])[CH3:25].[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:18]=[CH:19][C:20]([CH3:21])=[CH:22][CH:23]=3)(=[O:16])=[O:15])[CH2:11][N:10]2[C:39]([CH:36]2[CH2:37][CH2:38][N:35]2[CH:32]2[CH2:31][CH2:30][N:29]([C:27]([O:26][CH2:24][CH3:25])=[O:28])[CH2:34][CH2:33]2)=[O:40])=[O:8])[CH2:5][CH2:4]1)#[N:2]

Participants

3

Reactant 2

HCID 86692776Lithium 1-(1-(ethoxycarbonyl)piperidin-4-yl)azetidine-2-carboxylateHCID 86692783(2S,4R)-N-(1-cyanocyclopropyl)-4-tosylpyrrolidine-2-carboxamide

Product 1

HCID 71712115ethyl 4-(2-((2S,4R)-2-(1-cyanocyclopropylcarbamoyl)-4-tosylpyrrolidine-1-carbonyl)azetidin-1-yl)piperidine-1-carboxylate

Procedure

The reaction of (2S,4R)-N-(1-cyanocyclopropyl)-4-tosylpyrrolidine-2-carboxamide 7G 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-tosylpyrrolidine-1-carbonyl)azetidin-1-yl)piperidine-1-carboxylate 1:1 epimers as a white solid (70%). MS ISP (m/e): 572.2 (100) [(M+H)]+.

Sources & evidence

ORD record
ord-c2d928a83e634b50b8074270e9edbe35
Source dataset
uspto-grants-2014_08
Patent number
US08802665B2

Reaction notes

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