Lithium hydroxide, monohydrate → 4-(4-(Dibutylcarbamoyl)-1-phenethyl-1H-imidazol-2-yl)-3-((S)-3-(hydroxymethyl)-1,2,3,4-tetrahydroisoquinoline-2-carbonyl)benzoic acid

Participants

Reaction Steps

To a solution of methyl 4-(4-(dibutylcarbamoyl)-1-phenethyl-1H-imidazol-2-yl)-3-((S)-3-(hydroxymethyl)-1,2,3,4-tetrahydroisoquinoline-2-carbonyl)benzoate (110 mg, 0.169 mmol) in mixed solvents (2:2:1 THF/MeOH/H2O, 5.0 mL) was treated with LiOH H2O (21 mg, 0.507 mmol) at 0° C. The reaction mixture was allowed to warm to room temperature over 30 min and stirring was continued for 1 h. The reaction mixture was concentrated to give crude product, which was diluted with water and extracted with MTBE. The aqueous layer was neutralized with 0.5N HCl and extracted with DCM (3×). The combined organic layers were dried over Na2SO4 and concentrated in vacuo to give the title product (100 mg, 91%), which was used without purification. MS(ESI+) m/z 637.2 (M+H)+.

Provenance & Evidence