N-(tert-Butoxycarbonyl)-2,6-dimethyl-L-tyrosyl-N-{(2R)-2-[(benzyloxycarbonyl)amino]-3-phenylpropyl}-D-alaninamide → N-(tert-Butoxycarbonyl)-2,6-dimethyl-L-tyrosyl-N-{(2R)-2-amino-3-phenylpropyl}-D-alaninamide

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Reaction Steps

N-(tert-Butoxycarbonyl)-2,6-dimethyl-L-tyrosyl-N-{(2R)-2-[(benzyloxycarbonyl)amino]-3-phenylpropyl}-D-alaninamide (314 mg, 0.46 mmol) was dissolved in 5 mL of tetrahydrofuran and degassed by bubbling through argon gas for a few minutes. Palladium on charcoal (10% w/w, 5 mg) was added and the suspension stirred for 16 h at room temperature under 1 atmosphere of hydrogen pressure. The mixture was filtered through a short pad of celite, washed with 5 mL of tetrahydrofuran and evaporated under reduced pressure. The resulting residue was purified by column chromatography using 5% methanol in dichloromethane as eluant to provide the title compound as a clear oil (203 mg, 82%).

Provenance & Evidence