反应详情

A solution of 4-[3-amino-5-bromo-4-(3-nitro-benzyloxy)-phenyl]-2-methyl-5-oxo-7-propyl-1,4,5,6,7,8-hexahydro-quinoline-3-carbonitrile (1.15 g) and triethylamine (740 μl) in dichloromethane (20 ml) was treated with methanesulfonyl chloride (203 μl). After stirring for 18 h, the mixture was diluted with ethyl acetate and washed with water. The organic layer was dried (MgSO4), filtered and concentrated in vacuo. The crude N,N-bis-methanesulfonyl-aniline derivative was dissolved in THF (20 ml) and treated with 2N NaOH (3 ml). After 2 h, the mixture was quenched with sat. aq. NH4Cl and extracted with ethyl acetate. The organic layer was dried (MgSO4), filtered and concentrated in vacuo. The residue was purified by chromatography on silicagel in heptane/ethyl acetate 1/0→0/1 (v/v) as eluent.

1. washwashed with water
2. dry with materialThe organic layer was dried (MgSO4)
3. filtrationfiltered
4. concentrationconcentrated in vacuo
5. dissolutionThe crude N,N-bis-methanesulfonyl-aniline derivative was dissolved in THF (20 ml)
6. additiontreated with 2N NaOH (3 ml)
7. waitAfter 2 h
8. customthe mixture was quenched with sat. aq. NH4Cl
9. extractionextracted with ethyl acetate
10. dry with materialThe organic layer was dried (MgSO4)
11. filtrationfiltered
12. concentrationconcentrated in vacuo
13. customThe residue was purified by chromatography on silicagel in heptane/ethyl acetate 1/0→0/1 (v/v) as eluent