反应详情

O-(7-Azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate (554 mg) was added to a solution of 4-bromo-N2-methylbenzene-1,2-diamine (279 mg), diisopropylethylamine (0.727 mL) and (1RS,2SR)-2-(methoxycarbonyl)cyclopropanecarboxylic acid (200 mg) in DMF (5 mL) at room temperature. The mixture was stirred for 1 hr. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The obtained organic layer was washed with water and brine, dried over magnesium sulfate and concentrated in vacuo. The obtained residue was dissolved in acetic acid (5 mL), and the mixture was stirred at 80° C. for 1 hr. After concentration of the reaction mixture, saturated sodium hydrogen carbonate was added to the residue, and the mixture was extracted with ethyl acetate. The obtained organic layer was washed with water and brine, dried over magnesium sulfate and concentrated in vacuo. The obtained residue was purified by silica gel column chromatography (methanol/ethyl acetate) to give the title compound (80 mg) as a pale brown solid.

1. extractionthe mixture was extracted with ethyl acetate
2. washThe obtained organic layer was washed with water and brine
3. dry with materialdried over magnesium sulfate
4. concentrationconcentrated in vacuo
5. dissolutionThe obtained residue was dissolved in acetic acid (5 mL)
6. stirringthe mixture was stirred at 80° C. for 1 hr
7. additionAfter concentration of the reaction mixture, saturated sodium hydrogen carbonate was added to the residue
8. extractionthe mixture was extracted with ethyl acetate
9. washThe obtained organic layer was washed with water and brine
10. dry with materialdried over magnesium sulfate
11. concentrationconcentrated in vacuo
12. customThe obtained residue was purified by silica gel column chromatography (methanol/ethyl acetate)