Triphenylphosphine → HCID 131723005, compound

Participants

Reaction Conditions

Reaction Steps

The appropriate diastereomer of 2-cyclopropyl-3-(3,4-difluorophenyl)-3-hydroxypropionic acid N-((R)-(α-methylbenzyl)amide (1.1 g, 3.18 mmol), triphenylphosphine (1.7 g, 6.48 mmol), and diphenyl-phosphoryl azide (1.37 mL, 6.36 mmol) were combined in THF (30 mL) and cooled to −78° C. under nitrogen. Diethyl azodicarboxylate (1.2 mL, 7.63 mmol) was added and the mixture was stirred 1 hour at −78, 1 hour at 0° C. and 16 hours at ambient temperature. The reaction mixture was washed with saturated sodium bicarbonate and brine, dried the over sodium sulfate, filtered, and evaporated to dryness. The resulting oil was purified and separated by “flash” chromatography (98:2 of methylene chloride:ethyl ether). The product fractions were evaporated to dryness and the residue was reconcentrated from ethyl ether to yield the title compound as an oil.

Provenance & Evidence