(1S,2R)-(+)-2-Amino-1-cyclopentanecarboxylic acid hydrochloride → (1S,2R)-2-[({4-[(2-methylquinolin-4-yl)methoxy]phenyl}sulfonyl)amino]cyclopentanecarboxylic acid

HRID 736712Notes

Reaction equation

HRID 736712 reaction equation
Cl.[NH2:2][C@@H:3]1[CH2:7][CH2:6][CH2:5][C@@H:4]1[C:8]([OH:10])=[O:9].Cl.[CH3:12][C:13]1[CH:22]=[C:21]([CH2:23][O:24][C:25]2[CH:30]=[CH:29][C:28]([S:31](Cl)(=[O:33])=[O:32])=[CH:27][CH:26]=2)[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[N:14]=1>>[CH3:12][C:13]1[CH:22]=[C:21]([CH2:23][O:24][C:25]2[CH:30]=[CH:29][C:28]([S:31]([NH:2][C@@H:3]3[CH2:7][CH2:6][CH2:5][C@@H:4]3[C:8]([OH:10])=[O:9])(=[O:33])=[O:32])=[CH:27][CH:26]=2)[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[N:14]=1

Participants

3

Reactant 2

HCID 13831733(1S,2R)-(+)-2-Amino-1-cyclopentanecarboxylic acid hydrochlorideHCID 866078654-(2-Methylquinolin-4-ylmethoxy)benzenesulfonyl chloride hydrochloride

Product 1

HCID 68817773(1S,2R)-2-[({4-[(2-methylquinolin-4-yl)methoxy]phenyl}sulfonyl)amino]cyclopentanecarboxylic acidYield 87.6%

Procedure

According to the procedure of Example 10, Step 1, the reaction of 141 mg (0.85 mmol) of (+)-(1S,2R)-2-amino-1-cyclopentane-carboxylic acid hydrochloride with 400 mg (1.04 mmol) of 4-(2-methyl-quinolin-4-ylmethoxy)-benzenesulfonyl chloride hydrochloride provided 327.9 mg of (1S,2R)-2-[({4-[(2-methylquinolin-4-yl)methoxy]phenyl}sulfonyl)amino]cyclopentanecarboxylic acid in 86% yield. MS: 441.1 (M+H)+

Sources & evidence

ORD record
ord-c4aac4bf89d3488ca27ebc61723e1a53
Source dataset
uspto-grants-2009_09
Patent number
US07595327B2

Reaction notes

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