Trifluoroacetic acid → (3 S)-3-[N-((1-naphthyloxy)acetyl)leucinyl]amino-4-oxobutanoic acid semicarbazone

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Reaction Steps

To a solution of (3S)-3-[N-((1-naphthyloxy)acetyl)leucinyl]amino-4-oxobutanoic acid tert-butyl ester semicarbazone (0.366 g 0.69 mmol) in CH2Cl2(2.0 mL)-anisole(0.5 mL) at room temperature under nitrogen was added trifluoroacetic acid (2.0 mL). The resulting solution was stirred at room temperature for 3 hrs, evaporated to dryness and chased with toluene-CH2Cl2 (1:1). The residue was triturated with Et2O to give the title compound (0.354 g, 100%) as an off-white solid. TLC(AcOH-MeOH-CH2Cl2; 1:1:20) Rf=0.25. TLC(EtOAc-pyridine-AcOH-H2O; 60:20:5:10) Rf=0.48.

Provenance & Evidence