Trifluoroacetic acid → [(1S,6R)-7-Oxo-8-[(1R)-1-phenylethyl]-8-azabicyclo[4.3.0]non-3-en-1-yl]carboxylic acid

HRID 1917380ノート

反応式

HRID 1917380 の反応式
FC(F)(F)C(O)=O.C([O:12][C:13]([C@:15]12[CH2:23][N:22]([C@@H:24]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[CH3:25])[C:21](=[O:32])[C@@H:20]1[CH2:19][CH:18]=[CH:17][CH2:16]2)=[O:14])(C)(C)C>ClCCl>[O:32]=[C:21]1[N:22]([C@@H:24]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[CH3:25])[CH2:23][C@@:15]2([C:13]([OH:14])=[O:12])[C@H:20]1[CH2:19][CH:18]=[CH:17][CH2:16]2

参加物

4

反応物 2

HCID 6422Trifluoroacetic acidHCID 67490838[(1S,6R)-7-Oxo-8-[(1R)-1-phenylethyl]-8-azabicyclo[4.3.0]non-3-en-1-yl]carboxylic acid tert-butyl ester

生成物 1

HCID 67490831[(1S,6R)-7-Oxo-8-[(1R)-1-phenylethyl]-8-azabicyclo[4.3.0]non-3-en-1-yl]carboxylic acid収率 81.9%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

Trifluoroacetic acid (18.0 mL) was added to a solution of [(1S,6R)-7-oxo-8-[(1R)-1-phenylethyl]-8-azabicyclo[4.3.0]non-3-en-1-yl]carboxylic acid tert-butyl ester (2.04 g, 5.99 mmol) in dichloromethane (18.0 mL) with stirring under ice-cooling, and the mixture was stirred at room temperature for 1.5 hours. The reaction solution was concentrated under reduced pressure, and trifluoroacetic acid was azeotropically distilled with toluene (×3). A 1 mol/L sodium hydroxide solution (15.0 mL) was added to the resulting residue under ice-cooling, and the mixture was washed with diethyl ether (40 mL×2). The aqueous layer was made acidic with 1 mol/L hydrochloric acid (20 mL) under ice-cooling. Then, the precipitated crystals were collected by filtration and washed with 0.5 mol/L hydrochloric acid, ethyl acetate, and diethyl ether. The resulting crystals were dried under reduced pressure at 50° C. overnight to give 1.40 g of the title compound as white crystals. The aqueous layer of the filtrate was extracted with ethyl acetate (50 mL). The organic layers were combined, washed with water (150 mL) and brine (150 mL), and dried over anhydrous sodium sulfate. After filtration, the filtrate was concentrated under reduced pressure to give 250 mg of the title compound as white crystals.

後処理

  1. temperaturecooling
  2. stirringthe mixture was stirred at room temperature for 1.5 hours
  3. concentrationThe reaction solution was concentrated under reduced pressure, and trifluoroacetic acid
  4. distillationwas azeotropically distilled with toluene (×3)
  5. additionA 1 mol/L sodium hydroxide solution (15.0 mL) was added to the resulting residue under ice-
  6. temperaturecooling
  7. washthe mixture was washed with diethyl ether (40 mL×2)
  8. temperaturecooling
  9. filtrationThen, the precipitated crystals were collected by filtration
  10. washwashed with 0.5 mol/L hydrochloric acid, ethyl acetate, and diethyl ether
  11. customThe resulting crystals were dried under reduced pressure at 50° C. overnight

出典と根拠

ORDレコード
ord-7231cc44600546a298114339e7ed14d4
出典データセット
uspto-grants-2013_12
特許番号
US08618094B2

反応ノート

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