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 927854ノート

反応式

HRID 927854 の反応式
[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]

参加物

5

反応物 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-carboxylate2 回

生成物 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 acid収率 9.3%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 312751,4-Dioxane溶媒

反応条件

温度
80 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-297354883a7d4aacab5eb01cb8966de3
出典データセット
uspto-grants-2016_03
特許番号
US09290472B2

反応ノート

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