Methanol → HCID 59038381, compound

Participants

Reaction Steps

An aqueous 3N solution of sodium hydroxide (0.5 mL, 1.5 mmol) was added to a solution of (Z)-3-(2-amino-4-trifluoromethylthiazol-5-yl)-2-[[2-chloro-4-[[(3-hydroxybenzyl)amino]carbonyl]benzoyl]amino]propenoic acid methyl ester (Example 234; 90 mg, 0.16 mmol) in methanol (0.5 mL). The solution was stirred at room temperature for 16 h and then at 50° C. for 2 h. The reaction mixture was evaporated to dryness and the residue was dissolved in water (2 mL). 1N Hydrochloric acid solution (1.5 mL) was added and the resulting yellow solid was filtered off and washed well with water. The mixture of crude acids was purified by reverse phase HPLC and lyophilized to give (Z)-3-(2-amino-4-trifluoromethylthiazol-5-yl)-2-[[2-chloro-4-[[(3-hydroxybenzyl)amino]carbonyl]benzoyl]amino]propenoic acid (15 mg) and (Z)-2-[[2-chloro-4-[[(3-hydroxybenzyl)amino]carbonyl]benzoyl]amino]-3-(2-methylamino-4-trifluoromethylthiazol-5-yl)propenoic acid (15 mg).

Provenance & Evidence