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

HRID 736816Notes

Reaction equation

C([SiH](CC)CC)C.C([O:12][NH:13][C:14]([C@@:16]1([F:44])[CH2:20][CH2:19][CH2:18][C@H:17]1[NH:21][S:22]([C:25]1[CH:30]=[CH:29][C:28]([O:31][CH2:32][C:33]2[C:42]3[C:37](=[CH:38][CH:39]=[CH:40][CH:41]=3)[N:36]=[C:35]([CH3:43])[CH:34]=2)=[CH:27][CH:26]=1)(=[O:24])=[O:23])=[O:15])(C)(C)C>FC(F)(F)C(O)=O>[F:44][C@:16]1([C:14]([NH:13][OH:12])=[O:15])[CH2:20][CH2:19][CH2:18][C@H:17]1[NH:21][S:22]([C:25]1[CH:30]=[CH:29][C:28]([O:31][CH2:32][C:33]2[C:42]3[C:37](=[CH:38][CH:39]=[CH:40][CH:41]=3)[N:36]=[C:35]([CH3:43])[CH:34]=2)=[CH:27][CH:26]=1)(=[O:23])=[O:24]

Participants

Conditions

Temperature: 45 °C

Procedure

Triethylsilane (0.1 mL, 0.63 mmol) was added to a solution of (1R,2R)-N-(tert-butoxy)-1-fluoro-2-[({4-[(2-methylquinolin-4-yl)methoxy]phenyl}sulfonyl)amino]cyclopentane carboxamide (0.13 g, 0.25 mmol) in trifluoroacetic acid (2 mL). The reaction mixture was stirred at 45° C. for 7 h, and then concentrated and chased three times with methanol/toluene. The residue was purified using silica chromatography, eluting with a gradient of 5-10% MeOH/CH2Cl2 to afford (1R,2R)-1-fluoro-N-hydroxy-2-[({4-[(2-methylquinolin-4-yl)methoxy]phenyl}sulfonyl)amino]cyclopentanecarboxamide (0.106 g, 91%). MS: 474.1 (M+H)+

Workup

concentrationconcentrated
customThe residue was purified
washeluting with a gradient of 5-10% MeOH/CH2Cl2

Sources & evidence

ORD record: ord-315c1226389d4618bfeef9e5668f8e80
Source dataset: uspto-grants-2009_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07595327B2

Reaction notes

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