Ethanolamine → HCID 117701715, compound

Participants

Reaction Steps

To a solution of 7-(benzyloxy)-3-methyl-4-oxo-2-(1-propanoylpiperidin-4-yl)-4H-chromene-8-carboxylic acid (200 mg, 0.44 mmol) obtained in Example 35-1 in dichloromethane (4 mL), thionyl chloride (97 μL, 1.33 mmol) was added dropwise under cooling with ice. Then, a catalytic amount of dimethylformamide was added dropwise thereto, and the mixture was brought back to room temperature and stirred for 15 hours. The reaction solution was concentrated under reduced pressure, and then the residue was subjected to azeotropy with toluene (2 mL). Dichloromethane (4 mL) was added to the obtained residue. Triethylamine (93 μL, 0.67 mmol) and 2-aminoethanol (53 μL, 0.89 mmol) were added dropwise thereto under cooling with ice, and then the mixture was brought back to room temperature and stirred for 8 hours. Water was added to the reaction solution, followed by extraction with dichloromethane. Then, the organic layer was dried over sodium sulfate. The desiccant was filtered off, and then the filtrate was concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (chloroform/methanol=100/0→95/5) to obtain 144 mg of the title compound (yield: 66%).

Provenance & Evidence