Hydrochloric Acid → HCID 59038393, compound

Participants

Reaction Steps

An aqueous 1N solution of sodium hydroxide (0.55 mL, 0.55 mmol) was added to a suspension of rac.-(Z)-2-[[2-chloro-4-[(E)-hydroxy-3-(3-hydroxyphenyl)prop-2-en-1-yl]benzoyl]amino]-3-(2,4-dimethylthiazol-5-yl)propenoic acid methyl ester (Example 231; 90 mg, 0.175 mmol) in water (3 mL). The reaction mixture was stirred at room temperature for 5 h and then acidified with 1N hydrochloric acid solution (0.55 mL). The mixture was stirred for 30 min, then the solid was filtered off, washed with water, dried and evaporated. The crude acid was purified by reverse phase HPLC and lyophilized to give rac.-(Z)-2-[[2-chloro-4-[(E)-1-hydroxy-3-(3-hydroxyphenyl)prop-2-en-1-yl]benzoyl]amino]-3-(2,4-dimethylthiazol-5-yl)propenoic acid (43 mg, 51% yield) as a colorless solid.

Provenance & Evidence