Hydrochloric Acid → HCID 131733893, compound

Participants

Reaction Conditions

Reaction Steps

A 100 mL four-neck flask was charged with 5.0 g (24.5 mmol) of L-tryptophan, 7.0 g (24.5 mmol) of N-lauroyl-Ala-methyl, 70 g of cyclohexane and 2.8 g of methanol, and the flask contents were stirred under heating at 60° C. on an oil bath. Next, 9.5 g (49.0 mmol) of a 28% methanol solution of sodium methoxide as the base was added, and stirring was continued for 2 hours at about 60° C. The oil bath was then removed, 1.4 g of methanol was added, and the solution was allowed to cool to 25° C. This solution was added, under stirring at 35° C., to a mixed solution composed of 84 g of water, 91 g of methanol and 8.2 mL (49.0 mmol) of 6N hydrochloric acid. The pH was set to 6.7 by adding a 0.1N aqueous sodium hydroxide solution, following which the solvent was driven off by concentration under reduced pressure. Ethyl acetate and water were added to the residue, and the aqueous phase was extracted with ethyl acetate. The aqueous phase was concentrated under a reduced pressure to drive off the water and effect drying, thereby giving 9.2 g (yield, 83%; purity, 99%) of white crystals of free form of N-lauroyl-Ala-Trp.

Provenance & Evidence