Hydroxylamine → (1S,2R)-N-hydroxy-2-[({4-[(2-methylquinolin-4-yl)methoxy]phenyl}sulfonyl)amino]cyclopentanecarboxamide

HRID 736713Notes

Reaction equation

HRID 736713 reaction equation
[CH3:1][C:2]1[CH:11]=[C:10]([CH2:12][O:13][C:14]2[CH:19]=[CH:18][C:17]([S:20]([NH:23][C@@H:24]3[CH2:28][CH2:27][CH2:26][C@@H:25]3[C:29]([OH:31])=O)(=[O:22])=[O:21])=[CH:16][CH:15]=2)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1.[NH2:32][OH:33]>>[OH:33][NH:32][C:29]([C@H:25]1[CH2:26][CH2:27][CH2:28][C@H:24]1[NH:23][S:20]([C:17]1[CH:18]=[CH:19][C:14]([O:13][CH2:12][C:10]2[C:9]3[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=3)[N:3]=[C:2]([CH3:1])[CH:11]=2)=[CH:15][CH:16]=1)(=[O:22])=[O:21])=[O:31]

Participants

3

Reactant 2

HCID 787HydroxylamineHCID 68817773(1S,2R)-2-[({4-[(2-methylquinolin-4-yl)methoxy]phenyl}sulfonyl)amino]cyclopentanecarboxylic acid

Product 1

HCID 11854559(1S,2R)-N-hydroxy-2-[({4-[(2-methylquinolin-4-yl)methoxy]phenyl}sulfonyl)amino]cyclopentanecarboxamideYield 43%

Procedure

According to the procedure of Example 10, Step 2, the reaction of 321.4 mg (0.73 mmol) of (1S,2R)-2-[({4-[(2-methylquinolin-4-yl)methoxy]phenyl}sulfonyl)amino]cyclopentanecarboxylic acid with hydroxylamine provided 139.5 mg of (1S,2R)-N-hydroxy-2-[({4-[(2-methylquinolin-4-yl)methoxy]phenyl}sulfonyl)amino]cyclopentanecarboxamide with 43% yield. MS: 456.1 (M+H)+

Sources & evidence

ORD record
ord-4aa1c16a478b473da1d62517f91ab9cc
Source dataset
uspto-grants-2009_09
Patent number
US07595327B2

Reaction notes

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