反应详情

To a solution of 3.32 g of 2-(1-naphthylmethyl)-6-phenylhexanoic acid in 50 ml of dry acetonitrile were added 2.70 g of N,N'-disuccinimidylcarbonate and 2.0 ml of triethylamine with stirring at room temperature, and the mixture was stirred for 1 hour. The reaction mixture was added dropwise to a mixture of 2.42 g of L-histidine methyl ester dihydrochloride, 6 ml of N-methylmorpholine, 120 ml of dry N,N-dimethylformamide and 300 ml of dry chloroform, and the resulting mixture was stirred for 24 hours at 50° C. The reaction mixture was concentrated under reduced pressure and a 5% aqueous sodium bicarbonate solution was added to the residue and the mixture was extracted with ethyl acetate. The organic layer was washed with a saturated sodium chloride aqueous solution, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel flash column chromatography (eluent: chloroform/methanol=30/1 by volume) to obtain 3.06 g of N-[2-(1-naphthylmethyl)-6-phenylhexanoyl]-L-histidine methyl ester as a white powder.

1. stirringthe mixture was stirred for 1 hour
2. stirringthe resulting mixture was stirred for 24 hours at 50° C
3. concentrationThe reaction mixture was concentrated under reduced pressure
4. additiona 5% aqueous sodium bicarbonate solution was added to the residue
5. extractionthe mixture was extracted with ethyl acetate
6. washThe organic layer was washed with a saturated sodium chloride aqueous solution
7. dry with materialdried over anhydrous magnesium sulfate
8. concentrationconcentrated under reduced pressure
9. customThe residue was purified by silica gel flash column chromatography (eluent: chloroform/methanol=30/1 by volume)