反应详情

His(Trt)-OtBu (15.0 g, 33.1 mmol) and HOBt.H2O (5.13 g, 33.5 mmol) were added to N-palmitoyl-Gly (10.0 g, 31.9 mmol), and the whole was stirred while cooled with ice. Then, WSCD hydrochloride (6.42 g, 33.5 mmol) was added, and the whole was stirred while cooled with ice for 30 minutes and further stirred at room temperature for 18 hours. Water (500 ml) and ethyl acetate (400 ml) were added, and then, the aqueous phase was extracted with ethyl acetate (200 ml). The combined organic phase was successively washed with a saturated aqueous sodium hydrogen carbonate solution, a saturated saline solution, 10% citric acid aqueous solution, and a saturated saline solution, and dried over magnesium sulfate. The organic phase was concentrated under reduced pressure to give 28.1 g (118%) of a target compound as a pale yellow oily substance.

1. temperaturewhile cooled with ice
2. stirringthe whole was stirred
3. temperaturewhile cooled with ice for 30 minutes
4. stirringfurther stirred at room temperature for 18 hours
5. extractionthe aqueous phase was extracted with ethyl acetate (200 ml)
6. washThe combined organic phase was successively washed with a saturated aqueous sodium hydrogen carbonate solution
7. dry with materiala saturated saline solution, 10% citric acid aqueous solution, and a saturated saline solution, and dried over magnesium sulfate
8. concentrationThe organic phase was concentrated under reduced pressure