Water → HCID 118260146, compound

Participants

Reaction Steps

To a mixture of No. 6801976, tert-butyl (E)-(2S,3S)-3-[(S)-2-(4-but-2-ynyloxy-phenyl)-1-hydroxymethyl-ethylcarbamoyl]-2-hydroxy-2-(2-hydroxy-ethyl)-12-oxo-nonadec-4-enoate (304 mg, 0.45 mmol) and dichloromethane (15 mL) were added acetic anhydride (129 μL, 1.36 mmol) and pyridine (10 μL, 0.12 mmol), and the mixture was stirred at room temperature for 6 hours. Water was added and the mixture was extracted with dichloromethane, and dried over anhydrous sodium sulfate. The filtrate was then concentrated under reduced pressure. The resulting residue was left in a refrigerator overnight to obtain No. 6801977, tert-butyl (E)-(2S,3S)-2-(2-acetoxy-ethyl)-3-[(S)-1-acetoxymethyl-2-(4-but-2-ynyloxy-phenyl)-ethylcarbamoyl]-2-hydroxy-12-oxo-nonadec-4-enoate (328 mg, 96% yield, ESI (LC/MS positive mode) m/z 757 (M+H); Rt 3.37 min.). Formic acid (15 mL) was added to No. 6801977 (328 mg, 0.43 mmol) and the mixture was stirred at room temperature for 4 hours. After confirming the consumption of the starting materials by LCMS, formic acid was distilled off under reduced pressure. The residue was purified by preparative HPLC to obtain the title compound (35 mg, 11% yield, yellow oil).

Provenance & Evidence