反应详情

To a solution of (2-{3-[2-(2-tert-butoxycarbonylaminoethyl-sulfanylmethyl)-pyridin-3-yldisulfanyl]-pyridin-2-ylmethylsulfanyl}ethyl)carbamic acid tert-butyl ester (1.3 g, 0.0022 mol) in acetonitrile (120 mL) was added sodium borohydride (0.12 g, 0.003 mol), and the mixture was stirred at room temp. for 18 hours. (7R)-7-[(Z)-2-(2-amino-5-chlorothiazol-4-yl)-2-(triphenylmethoxyimino]-acetamido]-3-chloro-8-oxo-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylate diphenylmethyl ester (3.6 g, 0.0043 mol) was added in portions and the mixture was heated at reflux for 6 hours. The solvent was evaporated and the residue was partitioned between ethyl acetate (50 mL) and water (50 mL). The organic layer was separated, dried over anhydrous MgSO4 and concentrated. The residue was treated with diethyl ether (50 mL), and the solid that formed was filtered and dried to give 3.6 g of crude product. The crude product was purified by column chromatography on silica gel (100 g), eluting with hexane: ethyl acetate 1:1, to give the title compound (1.15 g).

1. temperaturethe mixture was heated
2. temperatureat reflux for 6 hours
3. customThe solvent was evaporated
4. customthe residue was partitioned between ethyl acetate (50 mL) and water (50 mL)
5. customThe organic layer was separated
6. dry with materialdried over anhydrous MgSO4
7. concentrationconcentrated
8. additionThe residue was treated with diethyl ether (50 mL)
9. customthe solid that formed
10. filtrationwas filtered
11. customdried
12. customto give 3.6 g of crude product
13. customThe crude product was purified by column chromatography on silica gel (100 g)
14. washeluting with hexane: ethyl acetate 1:1