Sodium Hydroxide → HCID 70079857, compound

Participants

Reaction Steps

A solution of [[(R,S)-methoxy-[N-(N-(benzoyl)-L-prolyl)aminobutyl]phosphinyl]methyl]-4-phenylbutanoyl-L-leucine N-phenylamide (101 mg, 0.14 mmol) in methanol (1 mL) was treated with 2N aqueous sodium hydroxide (0.5 mL) for 3 hours at room temperature. Additional 2N aqueous sodium hydroxide (0.5 mL) was then added, and the mixture was stirred overnight at room temperature. The solvent was removed by evaporation, and the residue was dissolved in water (25 mL). The aqueous solution was extracted with diethyl ether, acidified to ~pH 1 with 6N hydrochloric acid, and extracted with ethyl acetate (3×). The combined organic layers were washed With saturated brine solution, dried (magnesium sulfate), and evaporated. Purification was effected by reverse phase-high performance liquid chromatography using a Waters Prep Nova-Pak HR C18 6 mm column (19×300 mm) (detection at 220 nm; mobile phase: 57% acetonitrile containing 0.1% trifluoroacetic acid-43% water containing 0.1% trifluoroacetic acid; flow rate: 20 mL/min). Evaporation of appropriate fractions gave desired product as an amorphous solid; yield 47 mg; FAB-MS: m/z 703 (M+1),725 (M+Na), 741 (M+K). The 200 MHz NMR spectrum in methanol-d4 was in accord with the desired structure.

Provenance & Evidence