Hydrochloric Acid → HCID 53749380, compound

Participants

Reaction Steps

100 ml of methanol and 10 g (0.05 mol) of N,N-dimethylphenylalanine (prepared in accordance with Y. Ikutani, Bull. Chem. Soc. Jpn. 41, 1679 (1968)) are placed in a 350 ml sulfonating flask having an anchor mixer, thermometer, reflux condenser and gas introduction tube and, with stirring, saturated with HCl gas. The solution is stirred at reflux for 8 hours, then cooled, and the solvent is evaporated in a rotary evaporator. The residue is taken up in 250 ml of methylene chloride and washed first with 10% aqueous NaHCO3 solution and then with H2O until neutral. The reaction mixture is then dried over MgSO4, filtered and concentrated by evaporation. The residue is purified by flash chromatography (hexane/ethyl acetate=7:3), yielding 5.0 g of N,N-dimethylphenylalanine methyl ester in the form of a slightly yellow liquid. NMR analysis and IR spectrum agree with the said structure.

Provenance & Evidence