Ethyl Acetate → 4-[5-(2-cyclopentylacetamido)-1-ethylindol-3-ylmethyl]-3-methoxybenzoic N,N-diphenylcarbamic anhydride

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Reaction Steps

A solution of N,N-diphenylcarbamoylpyridinium chloride (311 mg) in methanol (1 ml) was added to a stirred solution of the acid (J) (450 mg) and sodium hydroxide (1 ml of a 1M aqueous solution) in methanol (4 ml) under an atmosphere of nitrogen. After stirring for 1.5 minutes, ethyl acetate and N,N-dimethylformamide (2 ml) were added and the mixture allowed to stir until all dissolved. The ethyl acetate solution was washed with water and saturated brine, dried (MgSO4) and evaporated to give a quantitative yield of 4-[5-(2-cyclopentylacetamido)-1-ethylindol-3-ylmethyl]-3-methoxybenzoic N,N-diphenylcarbamic anhydride (E) as a crusty foam; partial NMR: (80 MHz, DMSO-d6): 1.30(t, J=7.1 Hz, 2H, NCH2CH3), 3.84(s, 3H, OCH3), 3.94(s, 2H, ArCH2), 4.05(q, J=7.1 Hz, 2H, NCH2CH3), 7.41(s, 10H, NArH), 9.56(s, 1H, CONH).

Provenance & Evidence