Benzaldehyde → HCID 67272052, compound

Participants

Reaction Steps

A solution of 200 mg (0.5 mmol, 1 eq) of methyl 3-[2-amino-3′-(1-methyl-3-pentylureido)biphenyl-4-yl]propanoate (prepared in Example 52c) and 72 μL (0.70 mmol, 1.4 eq) of benzaldehyde in 4 ml of methanol in the presence of 63 mg (1.0 mmol, 2 eq) of sodium cyanoborohydride is stirred at room temperature for 16 hours. The reaction medium is hydrolyzed with ammonium chloride solution and then extracted with ethyl acetate. The organic phases are combined, washed with saturated sodium chloride solution and dried over sodium sulfate. The solvent is evaporated off and the residue is chromatographed on silica gel (70/30 heptane/ethyl acetate). 144 mg of methyl 3-[2-benzylamino-3′-(1-methyl-3-pentylureido)biphenyl-4-yl]propanoate are obtained in the form of a colorless oil. Yield=59%

Provenance & Evidence