Dicyclohexylcarbodiimide → HCID 54007225, compound

Participants

Reaction Conditions

Reaction Steps

In a 50 ml round flask were charged 191 mg (0.85 mmol) of (R)-4-hydroxybenzoic acid 1-(methoxycarbonyl)-ethyl ester as prepared in Example 1-2), 360 mg (0.935 mmol) of 4-(5-dodecyloxypyrimidin-2-yl)benzoic acid, 10.4 mg (0.085 mmol) of N,N-dimethyl-4-aminopyridine, and 20 ml of methylene chloride, followed by stirring at 25 ° C. To the mixture was added 193 mg (0.935 mmol) of DCC to conduct a reaction at 25° C. for 18 hours. After completion of the reaction, the solid was removed by filtration, and the filtrate was washed successively three times with 10 ml portions of water, three times with 10 ml portions of a 5% acetic acid aqueous solution, and three times with 10 ml portions of water. The organic solvent was removed under reduced pressure, and the residue was purified by silica gel column chromatography using a 20:1 (by volume) mixture of methylene chloride and diethyl ether. Recrystallization from hexane gave 110 mg (0.19 mmol) of Compound (35) in a yield of 22%.

Provenance & Evidence