Lithium hydroxide, monohydrate → (Z)-2-[[2-chloro-4-[[(3-hydroxybenzyl)amino]carbonyl]benzoyl]amino]-3-[4-(1-methylethyl)thiazol-5-yl]propenoic acid

Participants

Reaction Steps

A mixture of (Z)-2-[[2-chloro-4-[[(3-hydroxybenzyl)amino]carbonyl]benzoyl]amino]-3-[4-(1-methylethyl)thiazol-5-yl]propenoic acid methyl ester (Example 232; 75 mg, 0.146 mmol) and lithium hydroxide monohydrate (24 mg, 0.572 mmol) in methanol/tetrahydrofuran/water (2:2:1; 1.25 mL) was stirred at room temperature for 90 min. A further potion of lithium hydroxide monohydrate (6 mg, 0.143 mmol) was added and the reaction mixture was allowed to stir at room temperature for 65 h. After the reaction mixture was evaporated to dryness, water was added, followed by 1N hydrochloric acid solution (0.72 mL). The resulting colorless precipitate was filtered off, then was purified by reverse phase HPLC and lyophilized to afford (Z)-2-[[2-chloro-4-[[(3-hydroxybenzyl)amino]carbonyl]benzoyl]amino]-3-[4-(1-methylethyl)thiazol-5-yl]propenoic acid (42 mg, 58% yield) as a colorless powder.

Provenance & Evidence