Triethylamine → HCID 86754330, compound

Participants

Reaction Steps

A solution of 120 mg (0.23 mmol) of 4-[N-(3,5-bistrifluoromethyl-benzoyl)-N-methyl-amino]-5,5-diphenyl-pentanoic acid (example 32 h) and 45 μl (0.32 mmol) of triethylamine in 4 ml of N,N-dimethylformamide at 0° C. is treated with 36 μl (0.28 mmol) of (S)-leucinol, followed by 45 μl (0.28 mmol) of diethyl cyanophosphonate. After stirring for 4 h at room temperature, the reaction mixture is concentrated, diluted with ethyl acetate, and then washed with saturated sodium bicarbonate solution. The aqueous layer is further extracted with ethyl acetate (3×). The organic layers are combined, dried with sodium sulfate and concentrated. The residue is then purified by flash chromatography (98:2 to 95:5 methylene chloride/methanol) to give the title compound as a white solid (mixture of diastereomers). TLC: methylene chloride/methanol (95:5) Rf =0.22, 0.19

Provenance & Evidence