Dabco → Benzylurea

Participants

Reaction Steps

The compound obtained in Example 190, (1) (87 mg) was dissolved in toluene (2 ml), and benzyl isocyanate (14 μl) was added to the solution. 1,4-Diazabicyclo-[2,2,2]octane (4.7 μl) was added to the mixture under ice cooling, and the resulting mixture was warmed to room temperature and stirred for 2 hours. Ethyl acetate and saturated aqueous sodium hydrogencarbonate were added to the reaction mixture, the layers were separated, and the aqueous layer was extracted with ethyl acetate. The combined organic layer was washed with saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate, and filtered. The filtrate was concentrated under reduced pressure, and the resulting residue was purified by preparative thin layer chromatography (chloroform:methanol:28% aqueous ammonia=20:1:0.1) to obtain a benzylurea compound (62 mg). (2) By using the compound obtained in (1) mentioned above (62 mg) as a starting material, a deprotected compound (55 mg) was obtained in the same manner as that of Example 2, (2). (3) By using the compound obtained in (2) mentioned above (55 mg) as a starting material, the compound shown in Table 5 (20 mg) was obtained in the same manner as that of Example 11.

Provenance & Evidence