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Formic Acid → 4-[4-(tert-Butoxycarbonyl)phenyl]-2-[4-(methoxycarbonyl)benzyl]butanoic acid

HRID 1913774
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인쇄 미리보기

반응식

HRID 1913774 반응식
C(N(CC)CC)C.C(O)=O.[C:11]([O:15][C:16]([C:18]1[CH:23]=[CH:22][C:21]([CH2:24][CH2:25][C:26]([CH2:39][C:40]2[CH:45]=[CH:44][C:43]([C:46]([O:48][CH3:49])=[O:47])=[CH:42][CH:41]=2)(C(OCC=C)=O)[C:27]([O:29]CC=C)=[O:28])=[CH:20][CH:19]=1)=[O:17])([CH3:14])([CH3:13])[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>[C:11]([O:15][C:16]([C:18]1[CH:19]=[CH:20][C:21]([CH2:24][CH2:25][CH:26]([CH2:39][C:40]2[CH:45]=[CH:44][C:43]([C:46]([O:48][CH3:49])=[O:47])=[CH:42][CH:41]=2)[C:27]([OH:29])=[O:28])=[CH:22][CH:23]=1)=[O:17])([CH3:13])([CH3:14])[CH3:12]
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 4

HCID 284Formic AcidHCID 8471TriethylamineHCID 11776TriphenylphosphineHCID 59180509Diallyl {2-[4-(tert-butoxycarbonyl)phenyl]ethyl}[4-(methoxycarbonyl)benzyl]malonate

생성물 1

HCID 591805004-[4-(tert-Butoxycarbonyl)phenyl]-2-[4-(methoxycarbonyl)benzyl]butanoic acid수율 70.2%

시약·촉매·용매 2

HCID 167845
palladium(II) acetate
촉매
HCID 312751,4-Dioxane용매2회

반응 조건

온도
100 °C

실험 절차

A solution of 0.79 ml (5.66 mmol) of triethylamine and 0.16 ml (4.29 mmol) of formic acid in 10 ml of dioxane is added to a solution of 920 mg (1.71 mmol) of diallyl {2-[4-(tert-butoxycarbonyl)phenyl]ethyl}[4-(methoxycarbonyl)benzyl]malonate, 31.5 mg (0.12 mmol) of triphenylphosphine and 7.7 mg (0.03 mmol) of palladium acetate in 10 ml of dioxane at room temperature. The reaction mixture is then stirred at 100° C. for 12 hours. After conversion is complete, the reaction solution is cooled and the solvent is removed in vacuo. The resulting residue is purified by flash chromatography on silica gel (mobile phase: cyclohexane/ethyl acetate 4:1→1:1). 497 mg (1.2 mmol, 61% yield) of a colourless solid are obtained.

후처리

  1. temperaturethe reaction solution is cooled
  2. customthe solvent is removed in vacuo
  3. customThe resulting residue is purified by flash chromatography on silica gel (mobile phase: cyclohexane/ethyl acetate 4:1→1:1)

출처 및 근거

ORD 기록
ord-a52f1a2c8080404ba05a72dfe7f94282
출처 데이터셋
uspto-grants-2013_12
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08609727B2

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