Hydrochloric Acid → HCID 69316412, compound

Participants

Reaction Steps

Trifluoroacetic acid (3 ml) was added to a solution of N-t-butoxycarbonyl-3-[2-(2-naphthyl)ethoxy]-L-phenylalanine methyl ester (125 mg, 0.278 mmol) in methylene chloride (3 ml) under ice cooling and the mixture was stirred at the same temperature for 30 min. The solvent of the reaction mixture was distilled off at room temperature under reduced pressure. The residue was triturated with n-hexane and collected by filtration. The resultant solid was dissolved in tetrahydrofuran (1.2 ml)-water (0.6 ml). Lithium hydroxide mono-hydrate (41 mg, 0.973 mmol) was added to the solution with stirring under ice cooling and the mixture was reacted at the same temperature for 12 hrs. The reaction mixture was diluted with water (2 ml) and adjusted to pH 3-4 with 1N HCl. After the addition of water (25 ml), the mixture was stirred at room temperature for 1 hr. The precipitates were collected by filtration, washed with water and then dried under reduced pressure to give 3-[2-(2-naphthyl)ethoxy]-L-phenylalanine (55 mg, 59%) as colorless crystals.

Provenance & Evidence