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

HRID 1197046
ノート
印刷プレビュー

反応式

HRID 1197046 の反応式
[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
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 313Hydrochloric AcidHCID 1061PhosphateHCID 6097028Ammonium SulfateHCID 56608063HCID 56608063、化合物

生成物 1

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

試薬・触媒・溶媒 2

HCID 180
Acetone
溶媒
HCID 8857Ethyl Acetate溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-adec0ab354ad454baedb6ae74fe4392a
出典データセット
uspto-grants-1992_05
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US05116869

反応ノート

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