反应详情

温度

50 °C

To a solution of 3-tert-butoxycarbonyl-7-chloro-6-dimethylcarbamoylthio-2,3,4,5-tetrahydro-benzo[d]azepine (137 mg, 0.356 mmol) in methanol (2 mL) add potassium hydroxide pellets (640 mg, 11.4 mmol) and heat for 3 h at 50° C. Cool to ambient temperature, add saturated aqueous NH4Cl, extract three times with EtOAc, dry over anhydrous Na2SO4, and concentrate in vacuo. Dissolve the crude thiophenol thus obtained in dry DMF (2 mL), and add with stirring sodium hydride (18 mg, 0.713 mmol, 95% dispersion), followed by (S)-(+)-dihydro-5-(p-tolylsulfonyloxymethyl)-2-(3H)-furanone (144 mg, 0.533 mmol). Continue stirring overnight at ambient temperature, then dilute cautiously with EtOAc and cold saturated aqueous NH4Cl. Extract three times with EtOAc, dry over anhydrous Na2SO4, and concentrate in vacuo. Purify by chromatography on silica gel eluting with hexane/EtOAc (7:3) to give the title compound as a colorless oil.

1. temperatureCool to ambient temperature
2. extractionextract three times with EtOAc
3. dry with materialdry over anhydrous Na2SO4
4. concentrationconcentrate in vacuo
5. dissolutionDissolve the crude thiophenol
6. customthus obtained in dry DMF (2 mL)
7. extractionExtract three times with EtOAc
8. dry with materialdry over anhydrous Na2SO4
9. concentrationconcentrate in vacuo
10. customPurify by chromatography on silica gel eluting with hexane/EtOAc (7:3)