Water → (6,7-Bis(palmitoyloxy)-4-thiaheptanoyl)glycylglycylglycine t-butyl ester

To a solution of 6,7-bis(palmitoyloxy)-4-thiaheptanoic acid as obtained in Reference Example 4 (400 mg) and glycylglycylglycine t-butyl ester hydrochloride (149 mg) in dimethylformamide (6 ml), triethylamine (0.094 ml) and diethyl cyanophosphate (150 mg) were added at 0° C., followed by stirring at room temperature for 1 hour. After addition of water, the reaction mixture was extracted with chloroform. The extract was washed with a 5% aqueous solution of citric acid, a saturated aqueous solution of sodium hydrogen carbonate and saturated saline, and dried over anhydrous sodium sulfate, and the solvent was distilled off. The resulting residue was recrystallized (acetone-hexane) to yield the title compound (110 mg, yield 20%) as a wax-like substance.

1. additionwere added at 0° C.
2. extractionthe reaction mixture was extracted with chloroform
3. washThe extract was washed with a 5% aqueous solution of citric acid
4. dry with materiala saturated aqueous solution of sodium hydrogen carbonate and saturated saline, and dried over anhydrous sodium sulfate
5. distillationthe solvent was distilled off
6. customThe resulting residue was recrystallized (acetone-hexane)

ORD record

ord-f9bc5c355655454f9f491e3486211712

Source dataset

uspto-grants-1996_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05506267