(1R)-1-methyl-2-phenylcarbonyloxyethyl (2S)-2-[(tert-butoxy)carbonylamino]-3-[3,4-bis(phenylmethoxy)phenyl]propanoate → (1R)-1-Methyl-2-phenylcarbonyloxyethyl (2S)-3-(3,4-dihydroxyphenyl)-2-[(tert-butoxy)carbonylamino]propanoate

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Reaction Steps

To a solution of (1R)-1-methyl-2-phenylcarbonyloxyethyl (2S)-2-[(tert-butoxy)carbonylamino]-3-[3,4-bis(phenylmethoxy)phenyl]propanoate (5) (2.6 g, 4.85 mmol) in 40 mL of tetrahydrafuran, 10% Pd—C (200 mg) pre-mixed with 10 mL of methanol was added under a nitrogen atmosphere. The nitrogen atmosphere was exchanged with hydrogen using the evacuation refill cycle method. The mixture was stirred under hydrogen at room temperature for 2 hours. After filtration and washing with methanol, the filtrate was concentrated and chromatographed (silica gel, 30% ethyl acetate in hexane) to afford 1.87 g (100% yield) of the title compound (1). MS (ESI) m/z 460.20 (M+H)+ and 458.17 (M−H)−.

Provenance & Evidence