Sodium Hydroxide → HCID 18365441, compound

Participants

Reaction Steps

1-[4-(4-Fluoro-phenoxy)-benzenesulfonylamino]-cyclopentanecarboxylic acid benzyl ester (15 g, 32 mmole) in 75 mL THF was combined with 75 mL (150 mmole) 2N aqueous sodium hydroxide and stirred at reflux for 1 hour. The reaction was cooled to ambient temperature and diluted with 100 mL water and 100 mL ethyl acetate. The pH of the aqueous phase was adjusted to pH 1.2 and the ethyl acetate layer separated. The ethyl acetate layer was washed with 100 mL water and dried over magnesium sulfate. The ethyl acetate was stripped in vacuo and replaced with 75 mL methyl tert-butyl ether. The product was filtered and dried to yield 11.16 g (92%) of 1-[4-(4-fluoro-phenoxy) benzenesulfonylamino]-cyclopentanecarboxylic acid. 1H NMR (CDCl3) □ 7.71-7.78 (m, 2H), 6.88-7.04 (m, 6H), 5.04 (s, 1H), 2.01-2.13 (m, 2H), 1.92-1.98 (m, 2H), 1.44-1.68 (m, 4H).

Provenance & Evidence