Lithium 1-(1-(ethoxycarbonyl)piperidin-4-yl)azetidine-2-carboxylate → HCID 71712176, compound

HRID 2403192Notes

Reaction equation

HRID 2403192 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]=[CH:19][C:18]=3[O:23][CH3:24])(=[O:16])=[O:15])[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:17]3[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=3[O:23][CH3:24])(=[O:16])=[O:15])[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])[CH2:5][CH2:4]1)#[N:2]

Participants

3

Reactant 2

HCID 86692776Lithium 1-(1-(ethoxycarbonyl)piperidin-4-yl)azetidine-2-carboxylateHCID 86692784HCID 86692784, compound

Product 1

HCID 71712176HCID 71712176, compound

Procedure

The reaction of (2S,4R)-N-(1-cyanocyclopropyl)-4-(2-methoxyphenylsulfonyl)pyrrolidine-2-carboxamide 7C 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-methoxyphenylsulfonyl)pyrrolidine-1-carbonyl)azetidin-1-yl)piperidine-1-carboxylate 1:1 epimers as a white solid (76%). MS ISP (m/e): 588.2 (100) [(M+H)]+.

Sources & evidence

ORD record
ord-84f883afafc147b2b9bfccfdfd9a3523
Source dataset
uspto-grants-2014_08
Patent number
US08802665B2

Reaction notes

Loading…