3,4-Bis(cyclopropylmethoxy)benzoyl chloride → (+/-)-Acetic acid (1RS,3RS,4RS)-4-{[1-(3,4-bis-cyclopropylmethoxyphenyl)methanoyl]-amino}-3-(3,4-dimethoxyphenyl)cyclohexyl ester

Participants

Reaction Steps

9.5 mmol of (±)-acetic acid (1SR,3RS,4RS)-4-amino-3-(3,4-dimethoxyphenyl)cyclohexyl ester (compound B2) are dissolved in a mixture of 40 ml of methylene chloride and 10 ml of triethylamine and treated with 8.9 mmol of 3,4-dicyclopropylmethoxybenzoyl chloride. After stirring for 1 h at room temperature, the reaction mixture is concentrated and the residue chromatographed on silica gel using a mixture of petroleum ether/ethyl acetate/triethylamine in the ratio 4/4/1 as eluent. After concentration of the corresponding eluate fractions, 1.86 mmol of the title compound are obtained.

Provenance & Evidence