反应详情

温度

0 °C

To a solution of benzyl ((2R,3S)-1-(2,4-dimethoxybenzyl)-2-((E)-2-methoxyvinyl)-4-oxoazetidin-3-yl)carbamate (example 82, step 1, 1.44 g, 3.38 mmol) in DMF (33.8 ml) at −10° C. (salt-ice bath) was addeds sodium hydride (60%, 162 mg, 4.05 mmol). After stirring for 30 min, p-methoxybenzylchloride (506, μL, 3.71 mmol) was added. After warming to 0° C. and stirring for an additional 30 min, it was quenched with NH4Cl (aq, satd) then diluted with EtOAc and LiCl (5% aq). The layers were separated and aqueous layer was extracted with EtOAc (2×). The combined organic layers washed with LiCl (5% aq), brine, dried over Na2SO4 and concd in vacuo. The crude material was subjected to conditions described in example 82, step 2 then purified via silica gel chromatography (EtOAc-Hept, 0-70%) to afford the title compound (684 mg, 38%). LCMS: Rt=0.97 min, m/z=533.2 (M+1) Method 2m_acidic.

1. customat −10° C.
2. stirringstirring for an additional 30 min
3. customit was quenched with NH4Cl (aq, satd)
4. additionthen diluted with EtOAc and LiCl (5% aq)
5. customThe layers were separated
6. extractionaqueous layer was extracted with EtOAc (2×)
7. washThe combined organic layers washed with LiCl (5% aq), brine
8. dry with materialdried over Na2SO4 and concd in vacuo
9. customthen purified via silica gel chromatography (EtOAc-Hept, 0-70%)