Water → Benzyl carbamate

Participants

Reaction Steps

The compound obtained in Example 190, (1) (200 mg) was dissolved in tetrahydrofuran (2 ml), pyridine (58 μl) and benzyl chloroformate (68 μl) were added to the solution, and the resulting mixture was stirred at room temperature for 10 minutes. Distilled water and ethyl acetate were added to the reaction mixture, and the layers were separated. The organic layer was washed with saturated aqueous sodium chloride, then dried over anhydrous sodium sulfate, and filtered. The filtrate was concentrated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (ethyl acetate:methanol:28% aqueous ammonia=8:1:0.1) to obtain a benzyl carbamate compound (191 mg). (2) By using the compound obtained in (1) mentioned above (186 mg) as a starting material, a deprotected compound (156 mg) was obtained in the same manner as that of Example 4, (6). (3) By using the compound obtained in (2) mentioned above (60 mg) as a starting material, the compound shown in Table 5 (65 mg) was obtained in the same manner as that of Example 11.

Provenance & Evidence