Hydrochloric Acid → L-Phenylalanine, N-[(1,1-dimethylethoxy)carbonyl]-

Participants

Reaction Steps

To a solution of N-t-BOC-L-alanine 100-a (1.89 g, 9.99 mmol) and 1-hydroxybenzotriazole (270 mg, 2.00 mmol) in dimethylformamide (20 ml), a solution of dimethyl amine in 2.0 M tetrahydrofuran (7.50 ml, 15.0 mmol) and 1-ethyl-3-(3-dimethyl aminopropyl)-carbodiimide hydrochloride (2.30 g, 12.0 mmol) was added at room temperature and stirred for 4 hours. The mixture was mixed with water (50 ml) and extracted with ethyl acetate (100 ml). The extract was washed with water (20 ml) twice and brine (20 ml), and dried over sodium sulfate anhydrous. The residue, which was obtained from the mixture by evaporation in vacuo, was mixed with a solution of hydrogen chloride in 4M dioxane (25 ml, 100 mmol) and stirred for 45 min. The solvent was evaporated in vacuo to give a crude Compound 101-a, which was allowed to react without purification. In a manner similar to above, N-t-BOC-L-valine, N-t-BOC-L-leucine, N-t-BOC-L-isoleucine, N-t-BOC-L-phenylalanine and N□-t-BOC-Nlm-(benzyloxymethyl)-L-histidine each gave crude Compounds, 101-b to 101-f, respectively.

Provenance & Evidence