Triethylamine → HCID 86754459, compound

Participants

Reaction Steps

0.6 g of ethyl (3S)-3-(1-ethylphosphonomethyl-cyclopentane-1-carbonylamino)-2,3,4,5-tetrahydro-2-oxo-1H-1-benzazepine-1-acetate (preparation see Example 5) was dissolved in 20 ml of DMF with exclusion of moisture and then treated with 1.86 ml of triethylamine, 0.88 ml of pivaloyloxymethyl chloride and 0.1 g of dimethylaminopyridine. The reaction mixture was stirred overnight, the solvent was evaporated under reduced pressure and the residue was taken up in dichloromethane. The organic phase was washed with water and then dried over sodium sulfate. Concentration in vacuo yielded a crude product which for purification was chromatographed on 50 g of silica gel (eluent: initially n-hexane/ethyl acetate 3:7, the amount of ester gradually being increased to 100%). 188 mg of the title compound were obtained as an oil, IR=1740, 1650 cm-1 (CH2Cl2); [α]D20 =-124.1° (c=0.228 in methanol).

Provenance & Evidence