Cesium fluoride → (R)-3-{4-[1-(4-CyclohexylphenYl)-3-(3-hydroxymethyl-4-trifluoromethoxyphenyl)ureidomethyl]-benzoylamino}-2-hydroxypropionic acid

Participants

Reaction Conditions

Reaction Steps

(R)-3-{4-[3-[3-(tert-Butyldimethylsilanyloxymethyl)-4-trifluoromethoxyphenyl]-1-(4-cyclohexyl-phenyl)ureidomethyl]benzoylamino}-2-hydroxypropionic acid (17 mg, 0.023 mmol) was dissolved in acetonitrile:water (9:1) (2 mL) and caesium fluoride (35 mg, 0.35 mmol) added. The reaction mixture was stirred at 80° C. for 6 hours and additional amounts of caesium fluoride (35 mg) added. The mixture was stirred at 60° C. overnight, concentrated in vacuo and diluted with ethyl acetate (10 mL) and water (5 mL). The organic phase was washed with water (3×5 mL) and dried with magnesium sulphate and concentrated in vacua. The residue was purified by preparative HPLC affording the title compound.

Provenance & Evidence