Cispentacin → cis-2-[({4-[(2-Methylquinolin-4-yl)methoxy]phenyl}sulfonyl)amino]cyclopentanecarboxylic acid

HRID 736708Notes

Reaction equation

HRID 736708 reaction equation
[NH2:1][C@H:2]1[CH2:6][CH2:5][CH2:4][C@H:3]1[C:7]([OH:9])=[O:8].Cl.[CH3:11][C:12]1[CH:21]=[C:20]([CH2:22][O:23][C:24]2[CH:29]=[CH:28][C:27]([S:30](Cl)(=[O:32])=[O:31])=[CH:26][CH:25]=2)[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[N:13]=1>>[CH3:11][C:12]1[CH:21]=[C:20]([CH2:22][O:23][C:24]2[CH:29]=[CH:28][C:27]([S:30]([NH:1][C@H:2]3[CH2:6][CH2:5][CH2:4][C@H:3]3[C:7]([OH:9])=[O:8])(=[O:32])=[O:31])=[CH:26][CH:25]=2)[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[N:13]=1

Participants

3

Reactant 2

HCID 73305CispentacinHCID 866078654-(2-Methylquinolin-4-ylmethoxy)benzenesulfonyl chloride hydrochloride

Product 1

HCID 68817794cis-2-[({4-[(2-Methylquinolin-4-yl)methoxy]phenyl}sulfonyl)amino]cyclopentanecarboxylic acidYield 84.2%

Procedure

According to the procedure of Example 10, Step 1, the reaction of 322.9 mg (2.5 mmol) of cis-2-amino-1-cyclopentane-carboxylic acid with 960.7 mg of 4-(2-methyl-quinolin-4-ylmethoxy)-benzenesulfonyl chloride hydrochloride provided 927.7 mg of cis-2-[({4-[(2-methylquinolin-4-yl)methoxy]phenyl}sulfonyl)amino]cyclopentanecarboxylic acid in 84% yield. MS: 441.1 (M+H)+

Sources & evidence

ORD record
ord-7a8c8ec494e747ddae8aa5cb273f7bd6
Source dataset
uspto-grants-2009_09
Patent number
US07595327B2

Reaction notes

Loading…