Trifluoroacetic acid → 3-(3-Pyridyl)alanine [4-phenyl-1-(3-phenyl-propyl)-butyl]-amide

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Reaction Steps

N-tert-Butoxycarbonyl-3-(3-pyridyl)alanine [4-phenyl-1-(3-phenyl-propyl)-butyl]-amide (32) (2.08 g; 4.03 mmol) is dissolved in methylene chloride (40 mL) at ambient temperature. Trifluoroacetic acid (20 mL) is added in a slow stream, and the solution is stirred for 4 hours at ambient temperature. The solution is concentrated in vacuo at 40° C. The residue is dissolved in methylene chloride (200 mL) and poured onto saturated sodium bicarbonate solution. The pH is adjusted to 9 with saturated potassium carbonate solution. The mixture is shaken and the layers separated. The water layer is extracted with methylene chloride (3×50 mL). The combined organic extracts are washed with water, dried over MgSO4, filtered, and concentrated in vacuo affording the desired product (1.65 g) as an oil. ESMS: MH− 416.2

Provenance & Evidence