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Hydrochloric Acid → 2-Methylthio-5-(6-carboxyhexylidene)-4-(3-hydroxy-1-octenyl)-2-cyclopentenone

HRID 1197046
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HRID 1197046 반응식
[CH3:1][S:2][C:3]1[C:4](=[O:27])[C:5](=[CH:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][C:23]([O:25]C)=[O:24])[CH:6]([CH:8]=[CH:9][CH:10]([OH:16])[CH2:11][CH2:12][CH2:13][CH2:14][CH3:15])[CH:7]=1.P([O-])([O-])([O-])=O.Cl.S([O-])([O-])(=O)=O.[NH4+].[NH4+]>CC(C)=O.C(OCC)(=O)C>[CH3:1][S:2][C:3]1[C:4](=[O:27])[C:5](=[CH:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][C:23]([OH:25])=[O:24])[CH:6]([CH:8]=[CH:9][CH:10]([OH:16])[CH2:11][CH2:12][CH2:13][CH2:14][CH3:15])[CH:7]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 4

HCID 313Hydrochloric AcidHCID 1061PhosphateHCID 6097028Ammonium SulfateHCID 56608063HCID 56608063, 화합물

생성물 1

HCID 571118542-Methylthio-5-(6-carboxyhexylidene)-4-(3-hydroxy-1-octenyl)-2-cyclopentenone수율 58%

시약·촉매·용매 2

HCID 180
Acetone
용매
HCID 8857Ethyl Acetate용매

실험 절차

To a solution of 345 mg of 2-methylthio-5-(6-methoxycarbonylhexylidene)-4-(3-hydroxy-1-octenyl)-2-cyclopentenone obtained in Example 34 dissolved in 20 ml of acetone was added 220 ml of 0.1M phosphate buffer of pH 8. While the mixture was stirred, 24 mg of pig liver esterase was added thereto, and the mixture was stirred at 30-35° C. for 150 hours. After the pH was adjusted to 4 with 0.1N hydrochloric acid, ammonium sulfate was added to saturation and ethyl acetate was added, followed by filtration. The filtrate was extracted with ethyl acetate, and the organic layers were combined and washed with saturated aqueous sodium chloride. The product was dried over anhydrous magnesium sulfate, filtered and concentrated, followed by silica gel chromatography to give 193 mg (yield 58%) of 2-methylthio-5-(6-carboxyhexylidene)-4-(3-hydroxy-1-octenyl)-2-cyclopentenone.

후처리

  1. addition24 mg of pig liver esterase was added
  2. stirringthe mixture was stirred at 30-35° C. for 150 hours
  3. additionwas added
  4. filtrationfollowed by filtration
  5. extractionThe filtrate was extracted with ethyl acetate
  6. washwashed with saturated aqueous sodium chloride
  7. dry with materialThe product was dried over anhydrous magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated

출처 및 근거

ORD 기록
ord-adec0ab354ad454baedb6ae74fe4392a
출처 데이터셋
uspto-grants-1992_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05116869

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