Formic Acid → 4-[1-(2-Ethoxy-2-oxoethyl)cyclopropyl]-2-{2-[4-(methoxycarbonyl)phenyl]ethyl}butanoic acid

HRID 1920576노트

반응식

HRID 1920576 반응식
C(N(CC)CC)C.C(O)=O.[CH2:11]([O:13][C:14](=[O:46])[CH2:15][C:16]1([CH2:19][CH2:20][C:21]([CH2:34][CH2:35][C:36]2[CH:41]=[CH:40][C:39]([C:42]([O:44][CH3:45])=[O:43])=[CH:38][CH:37]=2)(C(OCC=C)=O)[C:22]([O:24]CC=C)=[O:23])[CH2:18][CH2:17]1)[CH3:12].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>O1CCOCC1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH2:11]([O:13][C:14](=[O:46])[CH2:15][C:16]1([CH2:19][CH2:20][CH:21]([CH2:34][CH2:35][C:36]2[CH:37]=[CH:38][C:39]([C:42]([O:44][CH3:45])=[O:43])=[CH:40][CH:41]=2)[C:22]([OH:24])=[O:23])[CH2:18][CH2:17]1)[CH3:12]

참가 물질

7

반응물 4

HCID 284Formic AcidHCID 8471TriethylamineHCID 11776TriphenylphosphineHCID 57965761Diallyl {2-[1-(2-ethoxy-2-oxoethyl)cyclopropyl]ethyl}{2-[4-(methoxycarbonyl)phenyl]ethyl}-malonate

생성물 1

HCID 579657474-[1-(2-Ethoxy-2-oxoethyl)cyclopropyl]-2-{2-[4-(methoxycarbonyl)phenyl]ethyl}butanoic acid

시약·촉매·용매 2

HCID 167845palladium(II) acetate촉매HCID 312751,4-Dioxane용매2회

반응 조건

온도
100 °C

실험 절차

At room temperature a solution of 0.6 ml (4.3 mmol) of triethylamine and 0.12 ml (3.25 mmol) of formic acid in 15 ml of dioxane is added to a solution of 650 mg (1.3 mmol) of diallyl {2-[1-(2-ethoxy-2-oxoethyl)cyclopropyl]ethyl}{2-[4-(methoxycarbonyl)phenyl]ethyl}malonate, 24 mg (0.09 mmol) of triphenylphosphine and 6 mg (0.026 mmol) of palladium acetate in 15 ml of dioxane. The reaction mixture is then stirred at 100° C. for 12 hours. After complete conversion, the reaction solution is cooled and the solvent is removed under reduced pressure. The residue is then taken up in ethyl acetate and water and acidified with 1 N hydrochloric acid, and the organic phase is removed. The aqueous phase is extracted three more times with ethyl acetate, and the organic phases are then combined, washed with saturated sodium chloride solution and dried over sodium sulfate. After filtration, the solution is concentrated under reduced pressure and the residue is purified by flash chromatography on silica gel (mobile phase: cyclohexane/ethyl acetate 4:1). This gives 406 mg (83% of theory) of a yellow oil.

후처리

  1. temperatureAfter complete conversion, the reaction solution is cooled
  2. customthe solvent is removed under reduced pressure
  3. customthe organic phase is removed
  4. extractionThe aqueous phase is extracted three more times with ethyl acetate
  5. washwashed with saturated sodium chloride solution
  6. dry with materialdried over sodium sulfate
  7. filtrationAfter filtration
  8. concentrationthe solution is concentrated under reduced pressure
  9. customthe residue is purified by flash chromatography on silica gel (mobile phase: cyclohexane/ethyl acetate 4:1)

출처 및 근거

ORD 기록
ord-2d4ae3fc8d8d4aa1bd3fdc80e110c925
출처 데이터셋
uspto-grants-2012_05
특허 번호
US08168821B2

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