Hydrochloric Acid → N-Palmitoyl-Gly-His(Trt)-OtBu

Participants

Reaction Steps

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.

Provenance & Evidence