methyl cis-(3aRS,9bRS)-5-acetyl-7-(2,2-dimethylpropionylamino)-1,2,3a,4,5,9b-hexahydro-furo[2,3-c]quinoline-6-carboxylate → methyl cis-(3aRS,9bRS)-5-acetyl-7-amino-1,2,3a,4,5,9b-hexahydrofuro[2,3-c]quinoline-6-carboxylate

HRID 927920노트

반응식

HRID 927920 반응식
[C:1]([N:4]1[C:13]2[C:8](=[CH:9][CH:10]=[C:11]([NH:18]C(=O)C(C)(C)C)[C:12]=2[C:14]([O:16][CH3:17])=[O:15])[C@H:7]2[CH2:25][CH2:26][O:27][C@H:6]2[CH2:5]1)(=[O:3])[CH3:2]>S(=O)(=O)(O)O.CO>[C:1]([N:4]1[C:13]2[C:8](=[CH:9][CH:10]=[C:11]([NH2:18])[C:12]=2[C:14]([O:16][CH3:17])=[O:15])[C@H:7]2[CH2:25][CH2:26][O:27][C@H:6]2[CH2:5]1)(=[O:3])[CH3:2]

참가 물질

4

반응물 1

HCID 86713286methyl cis-(3aRS,9bRS)-5-acetyl-7-(2,2-dimethylpropionylamino)-1,2,3a,4,5,9b-hexahydro-furo[2,3-c]quinoline-6-carboxylate2회

생성물 1

HCID 86713285methyl cis-(3aRS,9bRS)-5-acetyl-7-amino-1,2,3a,4,5,9b-hexahydrofuro[2,3-c]quinoline-6-carboxylate수율 77.4%

시약·촉매·용매 2

HCID 1118Sulfuric Acid촉매HCID 887Methanol용매

실험 절차

Concentrated sulfuric acid (5 drops) was added to a solution of methyl cis-(3aRS,9bRS)-5-acetyl-7-(2,2-dimethylpropionylamino)-1,2,3a,4,5,9b-hexahydro-furo[2,3-c]quinoline-6-carboxylate (Intermediate 30, 0.15 g) in methanol (5 mL) and the solution was stirred and heated at reflux for 48 hours. After cooling, the mixture was evaporated to low volume and the residue was dissolved in ethyl acetate and carefully washed with saturated aqueous sodium bicarbonate solution. The organic layer was filtered through a phase separator and the filtrate was evaporated to dryness to give methyl cis-(3aRS,9bRS)-5-acetyl-7-amino-1,2,3a,4,5,9b-hexahydrofuro[2,3-c]quinoline-6-carboxylate (0.09 g) as a brown gum.

후처리

  1. temperatureheated
  2. temperatureat reflux for 48 hours
  3. temperatureAfter cooling
  4. customthe mixture was evaporated to low volume
  5. dissolutionthe residue was dissolved in ethyl acetate
  6. washcarefully washed with saturated aqueous sodium bicarbonate solution
  7. filtrationThe organic layer was filtered through a phase separator
  8. customthe filtrate was evaporated to dryness

출처 및 근거

ORD 기록
ord-f54dc18af68f404f882cf295af3eba88
출처 데이터셋
uspto-grants-2016_03
특허 번호
US09290472B2

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