Trifluoroacetic acid → O-Benzyl-N-Methyl-L-Tyrosinamide

Participants

Reaction Steps

N-Boc-O-benzyl tyrosine methylamide (5.29 g, 13.8 mmol) was taken up in CH2Cl2 (100 ml). To the solution at 0° C. TFA (10 ml) was added dropwise and the solution allowed to warm to ambient temperature. After 4 hours the solvent and TFA were removed under vacuum. Any remaining TFA was quenched with saturated NaHCO3 solution (100 ml). The reaction mixture was extracted using CH2Cl2 (100 ml) and washed with saturated NaHCO3 solution (100 ml) and brine (100 ml). The CH2Cl2 layer was dried over Na2SO4 and the solvent was removed under vacuum to give a white solid, which was recrystallised from ethyl acetate/hexane to yield the title compound as a white crystalline solid (3.35 g, 85.4%).

Provenance & Evidence