Hydrochloric Acid → HCID 131733892, compound

Participants

Reaction Conditions

Reaction Steps

A 100 mL four-neck flask was charged with 1.25 g (6.1 mmol) of L-tryptophan, 2.0 g (6.1 mmol) of N-palmitoyl-Gly-methyl, 20 g of cyclohexane and 0.8 g of methanol, and stirred under heating at 60° C. on an oil bath. Next, 2.4 g (12.2 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, 0.4 g of methanol was added and, after being allowed to cool to 25° C., this solution was added, at 25° C. and under stirring, to a mixed solution composed of 30 g of water, 40 g of methanol and 2.0 mL (12.2 mmol) of 6N hydrochloric acid. After addition of the entire amount had been completed, the reaction solution was heated to 60° C. and stirred for 1 hour. The solution was then allowed to cool to 25° C. and the solid that deposited out was collected by filtration and washed with 6 g of water. Next, 30 g of water and 40 g of methanol were added to the resulting solid, and the system was heated to 60° C. and stirred for 1 hour. The system was then allowed to cool to 25° C. and the solid that deposited out was collected by filtration and washed with 6 g of water. The resulting solid was dried under reduced pressure, thereby giving 2.3 g (yield, 74%; purity, 90%) of white crystals of free form of N-palmitoyl-Gly-Trp.

Provenance & Evidence