Triethylamine → HCID 474086, compound

Participants

Reaction Conditions

Reaction Steps

In 7 ml of dry tetrahydrofuran was dissolved 700 mg (1.9 mmol) of the alcohol (137b), and after the solution was cooled to -40° C., 530 mg (2.8 mmol) of trichloroacetyl isocyanate was added, the temperature was elevated to room temperature. After 30 minutes, 2 ml of water and 1 ml of triethylamine were added and the mixture was stirred at room temperature for 3 days. The reaction mixture was diluted with water and extracted with ethyl acetate and the extract was washed with water, dried over sodium sulfate, filtered, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (3% methanol-ethyl acetate) and recrystallized from ethyl acetate-n-hexane to provide 705 mg (yield 90%) of Compound I-149 as crystals. mp 128-129° C.

Provenance & Evidence