Hydrochloric Acid → HCID 178467399, compound

Participants

Reaction Conditions

Reaction Steps

Sodium hydroxide (3.0 M in H2O, 5.98 mL, 17.93 mmol) was added to a solution of racemic butyl trans-4-[1-(5-bromo-1,3-thiazol-2-yl)-1-hydroxyethyl]cyclohexanecarboxylate (2.0 g, 5.12 mmol) in methanol (6 mL) and heated to 70° C. for 3 hour. Then, the reaction was cooled to room temperature and acidified with hydrochloric acid (3.0 M in H2O). Water (10 mL) was added and the mixture was stirred overnight at which point crystallization occurred. The reaction was filtered and the filter cake was washed with water and then dried under a nitrogen bag to afford racemic trans-4-[1-(5-bromo-1,3-thiazol-2-yl)-1-hydroxyethyl]cyclohexanecarboxylic acid as a white solid. MS ESI calc'd. for C12H17BrNO3S [M+H]+ 334, 336. found 334, 336. 1H NMR (600 MHz, DMSO-d6) δ 11.92 (s, 1H), 7.69 (s, 1H), 5.91 (s, 1H), 2.03-1.93 (m, 1H), 1.92-1.85 (m, 1H), 1.85-1.77 (m, 2H), 1.62-1.51 (m, 1H), 1.48-1.35 (m, 4H), 1.25-1.08 (m, 3H), 1.04-0.88 (m, 1H).

Provenance & Evidence