(1R,3S,4S)-3-[(5-chloro-thiophene-2-carbonyl)-amino]-4-hydroxy-cyclopentanecarboxylic acid methyl ester → 5-chloro-thiophene-2-carboxylic acid {(1S,2S,4R)-2-hydroxy-4-[2-methyl-4-(2-oxo-2H-pyridin-1-yl)-phenylcarbamoyl]-cyclopentyl}-amide

HRID 2244668Notes

Reaction equation

HRID 2244668 reaction equation
CO[C:3]([C@H:5]1[CH2:9][C@H:8]([OH:10])[C@@H:7]([NH:11][C:12]([C:14]2[S:15][C:16]([Cl:19])=[CH:17][CH:18]=2)=[O:13])[CH2:6]1)=[O:4].[NH2:20][C:21]1[CH:26]=[CH:25][C:24]([N:27]2[CH:32]=[CH:31][CH:30]=[CH:29][C:28]2=[O:33])=[CH:23][C:22]=1[CH3:34]>>[OH:10][C@H:8]1[CH2:9][C@H:5]([C:3](=[O:4])[NH:20][C:21]2[CH:26]=[CH:25][C:24]([N:27]3[CH:32]=[CH:31][CH:30]=[CH:29][C:28]3=[O:33])=[CH:23][C:22]=2[CH3:34])[CH2:6][C@@H:7]1[NH:11][C:12]([C:14]1[S:15][C:16]([Cl:19])=[CH:17][CH:18]=1)=[O:13]

Participants

3

Reactant 2

HCID 58826431(1R,3S,4S)-3-[(5-chloro-thiophene-2-carbonyl)-amino]-4-hydroxy-cyclopentanecarboxylic acid methyl esterHCID 668823531-(4-Amino-3-methylphenyl)pyridin-2(1H)-one

Product 1

HCID 160661595-chloro-thiophene-2-carboxylic acid {(1S,2S,4R)-2-hydroxy-4-[2-methyl-4-(2-oxo-2H-pyridin-1-yl)-phenylcarbamoyl]-cyclopentyl}-amide

Procedure

In analogy to example 1C, (1R,3S,4S)-3-[(5-chloro-thiophene-2-carbonyl)-amino]-4-hydroxy-cyclopentanecarboxylic acid methyl ester (example 1B) was reacted with 1-(4-amino-3-methyl-phenyl)-1H-pyridin-2-one to give 5-chloro-thiophene-2-carboxylic acid {(1S,2S,4R)-2-hydroxy-4-[2-methyl-4-(2-oxo-2H-pyridin-1-yl)-phenylcarbamoyl]-cyclopentyl}-amide. Off-white solid. MS: 472.4 ([M+H]+).

Sources & evidence

ORD record
ord-3915b8de317f4de6bc8d068996aea13e
Source dataset
uspto-grants-2010_03
Patent number
US07678917B2

Reaction notes

Loading…