反应详情

A 0.5M phosphate buffer solution (pH 6.5) was added to a solution of 6-[acetoxy-(10-benzyl-11-oxo-10,11-dihydro-dibenzo[b,f][1,4]oxazepin-8-yl)-methyl]-6-bromo-7oxo-4-thia-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-nitro-benzyl ester (0.210 g, 0.273 mmole) in THF, followed by 10% Pd—C (0.0546 g). The reaction mixture then was hydrogenated at 40 psi for three hours. Filtered through a celite pad and removed the THF by rotary evaporation, extracted the mixture with ethyl acetate and washed with water and brine. Dried the organic layer with sodium sulfate and filtered and concentrated. Dissolved the NaHCO3 with minimal amount of distal water and added it to the reaction mixture along with a small amount of ethyl acetate until the pH value reaches 7–8, evaporated the ethyl acetate. Purified with reverse phase column (MCI Gel CHP20P) with varying amounts of acetonitrile (0%-20%) in water. Removed the acetonitrile and water by rotary evaporation, and freeze-dried the compound. Obtained the desired material (yellow solid) in 24% yield.Mp: 179° C. 1H NMR (DMSO) δ 1.755–1.825 (s, 1H), 2.497–2.506 (d, 2H), 5.243–5.434 (m, 2H), 6.516–6.770 (m, 1H), 7.039–7.792 (m, 11H).

1. filtrationFiltered through a celite pad
2. customremoved the THF
3. customby rotary evaporation
4. extractionextracted the mixture with ethyl acetate
5. washwashed with water and brine
6. dry with materialDried the organic layer with sodium sulfate
7. filtrationfiltered
8. concentrationconcentrated
9. dissolutionDissolved the NaHCO3 with minimal amount of distal water
10. additionadded it to the reaction mixture along with a small amount of ethyl acetate until the pH value
11. customevaporated the ethyl acetate
12. customPurified with reverse phase column (MCI Gel CHP20P) with varying amounts of acetonitrile (0%-20%) in water
13. customRemoved the acetonitrile and water
14. customby rotary evaporation
15. customfreeze-dried the compound