Trimethyl orthoformate → HCID 11569806, compound

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Reaction Steps

The compound (124.0 mg) obtained in Example 77-5 was dissolved in methanol (1.5 ml). The reaction solution was added with the compound (45.2 mg) obtained in Example 14-7 and trimethyl orthoformate (0.2 ml) and the whole was stirred at room temperature for 2 hours. The reaction solution was cooled to 0° C. and added with sodium borohydride (27.8 mg) and the whole was stirred at room temperature for 10 minutes. The reaction solution was added with a saturated aqueous ammonium chloride solution and the whole was stirred at room temperature for 20 minutes. The reaction solution was added with distilled water and subjected to extraction with chloroform. The organic layer was washed with a saturated saline solution and dried with anhydrous sodium sulfate. After the drying agent was filtrated out, the resultant was concentrated under reduced pressure and the resultant residue was dissolved in methanol (2 ml). The reaction solution was added with 2-imidazole carboxaldehyde (53.9 mg) and sodium cyanoborohydride (59.3 mg) and solution was adjusted to pH 5 with acetic acid. The whole was stirred at room temperature for 15 hours. The reaction solution was added with a 1 mol/l sodium hydroxide aqueous solution and the whole was subjected to extraction with chloroform. The organic layer was washed with a saturated saline solution and dried with anhydrous sodium sulfate. After the drying agent was filtrated out, the resultant was concentrated under reduced pressure. The resultant residue was purified through silica gel column chromatography (chloroform/ethyl acetate) and treated with hydrochloric acid, thereby obtaining a hydrochloride (42.3 mg) of the subject compound as a pale-pink solid.

Provenance & Evidence