反应详情

To a stirred solution of methyl 2-hydroxy-4-(1-tert-butyloxycarbonyl-3-azetidinyloxy)benzoate from Step 3 above (1.30 g, 4.02 mmol) in DMF (40 mL) under N2 was added NaH (241 mg, 6.03 mmol). The reaction mixture was cooled, and CH3I (0.50 mL, 8.04 mmol) was added via syringe. The reaction mixture was allowed to warm to ambient temperature, then stirred for an additional 2 hours. The solvent was removed under reduced pressure and the residue was partitioned between ethyl acetate and aqueous NaHCO3. The ethyl acetate layer was dried (MgSO4), filtered, and evaporated under reduced pressure. The residue was purified using pressurized silica gel column chromatography, eluting with 20% ethyl acetate in hexanes. Methyl 2-methoxy-4-(1-tert-butyloxycarbonyl-3-azetidinyloxy)benzoate was obtained as a colorless oil which crystallized on standing overnight.

1. temperatureThe reaction mixture was cooled
2. customThe solvent was removed under reduced pressure
3. customthe residue was partitioned between ethyl acetate and aqueous NaHCO3
4. dry with materialThe ethyl acetate layer was dried (MgSO4)
5. filtrationfiltered
6. customevaporated under reduced pressure
7. customThe residue was purified
8. washeluting with 20% ethyl acetate in hexanes