Triethylamine → HCID 59750849, compound

Participants

Reaction Steps

Under a nitrogen atmosphere and at 0° C., triethylamine (157 μl, 1.13 mmol) and diphenylphosphoric azide (243 μl, 1.13 mmol) were added to a toluene solution (5 ml) of the 5-[(4-chlorophenyl)sulfonyl]-5-(2,5-difluorophenyl)valeric acid (400 mg, 1.03 mmol) obtained in Example 202. The resulting mixture was stirred at room temperature for 2 hours. The reaction mixture was heated under reflux for 3 hours. After cooling to room temperature and addition of 2-iodoethanol (160 μl, 2.06 mmol), the mixture was heated under reflux for further 1.5 hours. The reaction mixture diluted with ethyl acetate was then washed successively with a saturated aqueous solution of sodium bicarbonate, water, and brine, dried over magnesium sulfate and then, concentrated. The residue thus obtained was subjected to flash chromatography on a silica gel column, and the fraction obtained from the hexane:ethyl acetate=3:1 eluate was concentrated. The solid thus obtained was recrystallized from ethyl acetate-hexane, whereby the title compound (300 mg, 0.538 mmol, 52%) was obtained as colorless needle crystals.

Provenance & Evidence