반응 #803169

반응 방정식

methyl 6-(2,2-dimethylpropionylamino)-2-nitro-3-(2-oxopyrrolidin-1-yl)-benzoate

Intermediate 57

methyl 6-(2,2-dimethylpropionylamino)-2-nitro-3-(2-oxopyrrolidin-1-yl)-benzoate

→

methyl 6-(2,2-dimethylpropionylamino)-2,3-dihydro-1H-benzo[d]pyrrolo[1,2-a]imidazole-5-carboxylate

수율 79.7%

용매

acetic acid

반응 조건

후처리

1. 1
   온도After cooling
2. 2
   농축the mixture was concentrated in vacuo
3. 3
   workup.DISSOLUTIONthe residue was dissolved in ethyl acetate
4. 4
   여과2M sodium hydroxide solution and filtered through celite
5. 5
   건조The organic phase was dried (Na2SO4)
6. 6
   여과filtered
7. 7
   농축The filtrate was concentrated in vacuo
8. 8
   기타the residue was purified by chromatography on silica
9. 9
   세척eluting with a mixture of ethyl acetate and cyclohexane with a gradient of 50-100%
10. 10
    기타The product was repurified by chromatography on silica
11. 11
    세척eluting with a mixture of methanol and ethyl acetate with a gradient of 0-10%

실험 절차

A mixture of methyl 6-(2,2-dimethylpropionylamino)-2-nitro-3-(2-oxopyrrolidin-1-yl)-benzoate (Intermediate 57, 0.89 g), and iron powder (1.37 g) in acetic acid (25 mL) was stirred and heated at 115° C. for 2.5 hours. After cooling, the mixture was concentrated in vacuo and the residue was dissolved in ethyl acetate and 2M sodium hydroxide solution and filtered through celite. The organic phase was dried (Na2SO4) and filtered. The filtrate was concentrated in vacuo and the residue was purified by chromatography on silica, eluting with a mixture of ethyl acetate and cyclohexane with a gradient of 50-100%. The product was repurified by chromatography on silica, eluting with a mixture of methanol and ethyl acetate with a gradient of 0-10% to give methyl 6-(2,2-dimethylpropionylamino)-2,3-dihydro-1H-benzo[d]pyrrolo[1,2-a]imidazole-5-carboxylate (0.616 g) as an off-white solid.

출처