Sodium Hydroxide → HCID 23155584, compound

Participants

Reaction Steps

The compound (451.8 mg) obtained in Example 61-3 was dissolved in ethanol (18.1 ml) and added with a 1 mol/l sodium hydroxide aqueous solution (4.52 ml) and Raney nickel. The whole was stirred at room temperature for 20 hours under a hydrogen atmosphere. The reaction solution was filtrated through Celite and the filtrate was concentrated under reduced pressure. The residue was added with water and the whole was subjected to separation/extraction with chloroform. The organic layer was washed with a saturated saline solution and then dried with anhydrous sodium sulfate, followed by concentration under reduced pressure. The residue was again dissolved in methanol (22.1 ml) and added with 2-imidazole carboxaldehyde (194.0 mg) and trimethyl orthoformate (0.442 ml). The whole was stirred at room temperature for 1.5 hours. Subsequently, the solution was added with sodium borohydride (152.8 mg) under ice-cooling and the whole was stirred at room temperature for additional 30 minutes. The reaction solution was concentrated under reduced pressure. The residue was added with water and the whole was subjected to separation/extraction with chloroform. The organic layer washed with a saturated saline solution and dried with anhydrous sodium sulfate, followed by concentration under reduced pressure. The residue was purified through silica gel column chromatography (chloroform/methanol), thereby obtaining the subject compound (429.5 mg) as a yellow oily substance.

Provenance & Evidence