Sodium Hydroxide → (2R)-3-[[4-[(4-cyclohexylphenyl)-[[4-(trifluoromethylsulfanyl)phenyl]carbamoylamino]methyl]benzoyl]amino]-2-hydroxypropanoic acid

Participants

Reaction Steps

(R)-3-{4-[1-(4-Cyclohexylphenyl)-3-(4-trifluoromethylsulfanylphenyl)ureidomethyl]benzoylamino}-2-hydroxypropionic acid methyl ester (0.32 g, 0.508 mmol) was dissolved in ethanol (15 mL) and sodium hydroxide (4 N, 0.76 mL, 3.05 mmol) was added. The reaction mixture was stirred for 1.5 hour. The reaction was evaporated and added water (15 mL) and acidified with hydrochloric acid (4 N, 0.8 mL). The mixture was extracted with ethyl acetate (20 mL). The aqueous phase was extracted once more with ethyl acetate (15 mL) and the combined organic phases were washed with water (3×10 mL), dried over magnesium sulphate, filtered and concentrated to give the title compound (0.3 g).

Provenance & Evidence