4-Methylmorpholine → HCID 86641344, compound

Participants

Reaction Conditions

Reaction Steps

N-Methylmorpholine (22 μl) was added to a mixture composed of the above {4-[bis(tert-butoxycarbonyl)amino]-2-[(4-methoxy-3,5-dimethylpyridin-2-yl)methyl]-2,7-dihydro-6-thia-1,2,3,5-tetraazabenzo[cd]azulen-8-yl}acetic acid (60 mg) and tetrahydrofuran (2 ml). Then, isobutyl chloroformate (39 μl) was added and the mixture was stirred at 0° C. for one hour. N-Methylmorpholine (44 μl) and isobutyl chloroformate (39 μl) were added to the reaction mixture, and the mixture was further stirred at 0° C. for 30 minutes. Water was added to the reaction mixture, followed by extraction with ethyl acetate. The organic layer was dried over sodium sulfate and filtered. Then, the filtrate was concentrated under reduced pressure. Tetrahydrofuran (2 ml) and water (0.4 ml) were added to the resulting residue. Then, sodium borohydride (15 mg) was added under ice-cooling, and the mixture was stirred at 0° C. for one hour. Methanol (2 ml) was added dropwise to the reaction mixture. Then, the mixture was returned to room temperature and stirred for 16 hours. Water was added to the reaction mixture, followed by extraction with ethyl acetate. The organic layer was washed with brine, and then dried over sodium sulfate and filtered. Then, the filtrate was concentrated under reduced pressure. The resulting residue was purified by silica gel thin-layer chromatography (hexane-ethyl acetate) to obtain the title compound (16 mg, 27%) as an oil.

Provenance & Evidence