Lithium Hydroxide → cis-(3aRS,9bRS)-7-[2-((Z)-3-diethylaminoprop-1-enyl)-4-fluorobenzenesulfonylamino]-1,2,3a,4,5,9b-hexahydrofuro[2,3-c]quinoline-6-carboxylic acid

HRID 927854노트

반응식

HRID 927854 반응식
[OH-].[Li+].C([N:6]1[C:15]2[C:10](=[CH:11][CH:12]=[C:13]([NH:20][S:21]([C:24]3[CH:29]=[CH:28][C:27]([F:30])=[CH:26][C:25]=3/[CH:31]=[CH:32]\[CH2:33][N:34]([CH2:37][CH3:38])[CH2:35][CH3:36])(=[O:23])=[O:22])[C:14]=2[C:16]([O:18]C)=[O:17])[C@H:9]2[CH2:39][CH2:40][O:41][C@H:8]2[CH2:7]1)(=O)C>O1CCOCC1.O>[CH2:37]([N:34]([CH2:35][CH3:36])[CH2:33]/[CH:32]=[CH:31]\[C:25]1[CH:26]=[C:27]([F:30])[CH:28]=[CH:29][C:24]=1[S:21]([NH:20][C:13]1[C:14]([C:16]([OH:18])=[O:17])=[C:15]2[C:10]([C@H:9]3[CH2:39][CH2:40][O:41][C@H:8]3[CH2:7][NH:6]2)=[CH:11][CH:12]=1)(=[O:23])=[O:22])[CH3:38]

참가 물질

5

반응물 2

HCID 3939Lithium HydroxideHCID 86713243methyl cis-(3aRS,9bRS)-5-acetyl-7-[2-((Z)-3-diethylaminoprop-1-enyl)-4-fluorobenzenesulfonylamino]-1,2,3a,4,5,9b-hexahydrofuro[2,3-c]quinoline-6-carboxylate2회

생성물 1

HCID 86713242cis-(3aRS,9bRS)-7-[2-((Z)-3-diethylaminoprop-1-enyl)-4-fluorobenzenesulfonylamino]-1,2,3a,4,5,9b-hexahydrofuro[2,3-c]quinoline-6-carboxylic acid수율 9.3%

시약·촉매·용매 2

HCID 962Water용매HCID 312751,4-Dioxane용매

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온도
80 °C

실험 절차

Lithium hydroxide (0.09 g) was added to a solution of methyl cis-(3aRS,9bRS)-5-acetyl-7-[2-((Z)-3-diethylaminoprop-1-enyl)-4-fluorobenzenesulfonylamino]-1,2,3a,4,5,9b-hexahydrofuro[2,3-c]quinoline-6-carboxylate (Intermediate 27, 0.06 g) in a mixture of dioxane (5 mL) and water (1 mL) and the mixture was stirred and heated at 80° C. overnight. The mixture was then irradiated in the microwave at 150° C. for 30 minutes and then at 180° C. for 30 minutes. After cooling, the mixture was filtered and the filtrate was acidified by addition of formic acid (1 mL) and then evaporated to dryness. The residue was purified by preparative HPLC (C18) eluting with a mixture of acetonitrile and water, containing 0.1% formic acid, with a gradient of 10-98%. The isolated product was dissolved in DCM and evaporated to dryness then dissolved in ether and evaporated to dryness to give cis-(3aRS,9bRS)-7-[2-((Z)-3-diethylaminoprop-1-enyl)-4-fluorobenzenesulfonylamino]-1,2,3a,4,5,9b-hexahydrofuro[2,3-c]quinoline-6-carboxylic acid (0.005 g) as a white solid.

후처리

  1. customThe mixture was then irradiated in the microwave at 150° C. for 30 minutes
  2. temperatureAfter cooling
  3. filtrationthe mixture was filtered
  4. additionthe filtrate was acidified by addition of formic acid (1 mL)
  5. customevaporated to dryness
  6. customThe residue was purified by preparative HPLC (C18)
  7. washeluting with a mixture of acetonitrile and water
  8. additioncontaining 0.1% formic acid
  9. dissolutionThe isolated product was dissolved in DCM
  10. customevaporated to dryness
  11. dissolutionthen dissolved in ether
  12. customevaporated to dryness

출처 및 근거

ORD 기록
ord-297354883a7d4aacab5eb01cb8966de3
출처 데이터셋
uspto-grants-2016_03
특허 번호
US09290472B2

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