(1R,2S)-2-Aminocyclohexane-1-carboxylic acid → cis-2-[({4-[(2-Methylquinolin-4-yl)methoxy]phenyl}sulfonyl)amino]cyclohexanecarboxylic acid

HRID 736710Notes

Reaction equation

HRID 736710 reaction equation
[NH2:1][C@H:2]1[CH2:7][CH2:6][CH2:5][CH2:4][C@H:3]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:1][C@H:2]3[CH2:7][CH2:6][CH2:5][CH2:4][C@H:3]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 2724639(1R,2S)-2-Aminocyclohexane-1-carboxylic acidHCID 866078654-(2-Methylquinolin-4-ylmethoxy)benzenesulfonyl chloride hydrochloride

Product 1

HCID 68821094cis-2-[({4-[(2-Methylquinolin-4-yl)methoxy]phenyl}sulfonyl)amino]cyclohexanecarboxylic acidYield 28.5%

Procedure

According to the procedure of Example 10, Step 1, the reaction of 429.6 mg (3 mmol) of cis-2-amino-1-cyclohexane-carboxylic acid with 1.15 g of 4-(2-methyl-quinolin-4-ylmethoxy)-benzenesulfonyl chloride hydrochloride provided 387.9 mg of cis-2-[({4-[(2-methylquinolin-4-yl)methoxy]phenyl}sulfonyl)amino]cyclohexanecarboxylic acid in 28% yield. MS: 455.1 (M+H)+

Sources & evidence

ORD record
ord-cb34e8acdafd4748b0644d48fb7522d9
Source dataset
uspto-grants-2009_09
Patent number
US07595327B2

Reaction notes

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