Sodium Hydroxide → (E)-5-(3-Phenylsulfamoylphenyl)pent-2-en-4-ynoic acid

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Reaction Steps

To a solution of E-5-(3-phenylsulfamoylphenyl)pent-2-en-4-ynoic acid methyl ester (55a) (0.34 g, 1 mmol) in methanol (3 ml) 1N solution of sodium hydroxide (3 ml) was added and the mixture was stirred at ambient temperature for 3 hours. Methanol was removed under reduced pressure, to the residue water (5 ml) was added and the mixture was acidified with 3% HCl. The precipitate was filtered, washed with water, and dried to give the title compound (0.31 g, 95%) as white crystals. M.p. 188-190° C. 1H NMR (DMSO-d6, HMDSO) δ: 6.36 (1H, d, J=15.8 Hz, CH); 6.92 (1H, d, J=15.8 Hz, CH); 7.01-7.36 (5H, m, C6H5); 7.38-7.89 (4H, m, C6H4); 10.32 (1H, s, NH).

Provenance & Evidence