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

HRID 1917380노트

반응식

HRID 1917380 반응식
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

참가 물질

4

반응물 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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-7231cc44600546a298114339e7ed14d4
출처 데이터셋
uspto-grants-2013_12
특허 번호
US08618094B2

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