Sodium Hydroxide → HCID 24958677, compound

Participants

Reaction Steps

To a solution of {2-[2-(2,4-Difluoro-phenoxy)-2-methyl-butyrylamino]-thiazol-4-yl}-acetic acid ethyl ester (0.202 g, 0.51 mmol) in MeOH (3 ml) and water (1.5 ml). NaOH (0.041 g, 1.1 mmol) was added and stirred at room temperature for 16 hrs. The organic solvent was evaporated and residue was diluted with water (2 ml) and acidified (pH˜2) with 5% HCl. The aqueous layer was extracted with ethyl acetate (2×10 ml) and organic layer was washed with saturated brine (10 ml). The organic layer was dried over Na2SO4 and evaporated under reduced pressure to obtain crude product which was solidified by triturating with hexane to afford {2-[2-(2,4-Difluoro-phenoxy)-2-methyl-butyrylamino]-thiazol-4-yl}-acetic acid (0.158 g, 84%). 1H NMR (400 MHz, CDCl3): δ1.03 (t, J=7.6 Hz, 3H), 1.44 (s, 3H), 1.86-1.9 (m, 1H), 2.05-2.09 (m, 1H), 3.78 (s, 2H), 6.78 (s, 1H), 6.80-6.84 (m, 1H), 6.88-6.93 (m, 1H), 7.0-7.06 (m, 1H), 10.6 (s, 1H), MS (EI) m/z: 371.00 (M+1) and mp: 148-149° C.

Provenance & Evidence