Hydrochloric Acid → (Z)-2-[[2-chloro-4-[[(3-hydroxybenzyl)amino]carbonyl]benzoyl]amino]-3-(2-ethyl-4-methylthiazole-5-yl)propenoic acid

Participants

Reaction Steps

A solution of lithium hydroxide monohydrate (100 mg, 2.4 mmol) in water (3 mL) was added to a solution of (Z)-3-(2-ethyl-4-methylthiazole-5-yl)-2-[[4-[[(3-hydroxybenzyl)amino]carbonyl]-2-methylbenzoyl]amino]propenoic acid methyl ester (Example 216; 120 mg, 0.2 mmol) in tetrahydrofuran/methanol (3:1; 12 mL) and the reaction was allowed to stir at room temperature overnight. Water (50 mL) and 1N hydrochloric acid solution (3 mL) were added and the mixture was extracted with ethyl acetate (2×50 mL). The ethyl acetate layers were concentrated and purified by HPLC to give (Z)-2-[[2-chloro-4-[[(3-hydroxybenzyl)amino]carbonyl]benzoyl]amino]-3-(2-ethyl-4-methylthiazole-5-yl)propenoic acid (105 mg, 90% yield) as a colorless solid, mp>200° C.

Provenance & Evidence