Triethylamine → HCID 86641345, compound

Participants

Reaction Conditions

Reaction Steps

A mixture composed of methyl {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}acetate of Example 111 (121 mg), diphenylphosphoryl azide (64 μl), triethylamine (69 μl) and benzene (2 ml) was heated with stirring at a bath temperature of 55° C. for two hours. The reaction mixture was concentrated under reduced pressure. Tetrahydrofuran (8 ml) and a 1 N sodium hydroxide solution (4 ml) were added to the resulting residue, and the mixture was heated with stirring at a bath temperature of 55° C. for one hour. A 0.2 N sodium hydroxide solution was added, followed by extraction with ethyl acetate. The organic layer was dried over sodium sulfate and filtered. Then, the filtrate was concentrated under reduced pressure. The concentrated residue was purified by silica gel column chromatography (chloroform-methanol) to obtain the title compound (41 mg) as a brown oil. Although the product contained impurities, it was directly used for the next reaction without further purification.

Provenance & Evidence