Sodium Hydroxide → HCID 59038348, compound

Participants

Reaction Steps

A solution of 1N sodium hydroxide (0.16 mL, 0.16 mmol) was added to a solution of (Z)-2-[[2-bromo-4-[[(3-hydroxybenzyl)amino]carbonyl]benzoyl]amino]-3-(thiazol-2-yl)propenoic acid methyl ester (Example 153; 39.3 mg, 0.076 mmol) in tetrahydrofuran/methanol (2:1; 0.25 mL). After the solution had been allowed to stir at room temperature for 16 h, a second portion of 1N sodium hydroxide solution (0.05 mL) was added and the reaction was allowed to proceed for another 24 h at ambient temperature. The solvent was evaporated using a rotary evaporator then high vacuum. The de-esterification had not gone to completion, so the residue was re-dissolved in tetrahydrofuran/methanol (2:1; 0.25 mL) and treated with a solution of 1N sodium hydroxide (0.16 mL, 0.16 mmol). The reaction mixture was stirred for 16 h and after the solvents were removed in vacuo, the residue was purified by HPLC to give (Z)-2-[[2-bromo-4-[[(3-hydroxybenzyl)amino]carbonyl]benzoyl]amino]-3-(thiazol-2-yl)propenoic acid (14.8 mg, 39%).

Provenance & Evidence