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Acetone → 7-(3-Hydroxy-5-oxo-1-cyclopenten-1-yl)-heptanoic acid p-benzoylaminophenyl ester

HRID 1105643
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인쇄 미리보기

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HRID 1105643 반응식
[OH:1][CH:2]1[CH2:6][C:5](=[O:7])[C:4]([CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][C:14]([OH:16])=[O:15])=[CH:3]1.CC(C)=O.ClC(OCC(C)C)=O.[C:29]([NH:37][C:38]1[CH:43]=[CH:42][C:41](O)=[CH:40][CH:39]=1)(=[O:36])[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1>N1C=CC=CC=1.C(N(CC)CC)C>[C:29]([NH:37][C:38]1[CH:43]=[CH:42][C:41]([O:15][C:14](=[O:16])[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][C:4]2[C:5](=[O:7])[CH2:6][CH:2]([OH:1])[CH:3]=2)=[CH:40][CH:39]=1)(=[O:36])[C:30]1[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=1
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참가 물질

7

반응물 4

HCID 180AcetoneHCID 62365Isobutyl chloroformateHCID 459327Benzamide, N-(4-hydroxyphenyl)-HCID 3690897ACMC-20apjz

생성물 1

HCID 571537857-(3-Hydroxy-5-oxo-1-cyclopenten-1-yl)-heptanoic acid p-benzoylaminophenyl ester

시약·촉매·용매 2

HCID 1049Pyridine
용매
HCID 8471Triethylamine용매

반응 조건

온도
25 °C

실험 절차

0.326 g. of 7-(3-Hydroxy-5-oxo-1-cyclopenten-1-yl)-heptanoic acid were dissolved in 20 ml. of dry acetone. At -20° C., 0.23 ml. of triehtylamine were added and then 0.216 ml. isobutyl chloroformate. After 5 minutes, the temperature was permitted to increase to 25° C., and 0.4 g. of p-benzoylaminophenol dissolved in 10 ml. of dry pyridine was added dropwise. After 2 hours, the solvent was distilled off; the residue was extracted in ethyl acetate; the organic phase was washed with water and dried over sodium sulphate. The solvent was distilled off. After chromatographic purification of the residue (silica gel/ethyl acetate), 7-(3-hydroxy-5-oxo-1-cyclopenten-1-yl)-heptanoic acid p-benzoylaminophenyl ester (m.p. 168°-169° C.) was obtained.

후처리

  1. customAt -20° C.
  2. waitAfter 2 hours
  3. distillationthe solvent was distilled off
  4. extractionthe residue was extracted in ethyl acetate
  5. washthe organic phase was washed with water
  6. dry with materialdried over sodium sulphate
  7. distillationThe solvent was distilled off
  8. customAfter chromatographic purification of the residue (silica gel/ethyl acetate)

출처 및 근거

ORD 기록
ord-1f90fd7d2f6f452a9a05e11f7cf6d1af
출처 데이터셋
uspto-grants-1982_01
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US04309441

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