Water → HCID 15673225、化合物

HRID 1196458

反応式

HRID 1196458 の反応式
[SH:1][C@@H:2]([CH2:6][CH:7]([CH3:9])[CH3:8])[C:3]([OH:5])=[O:4].[C:10]1(C)C=CC(S(O)(=O)=O)=C[CH:11]=1.O>C(O)C.C(Cl)(Cl)Cl>[SH:1][C@@H:2]([CH2:6][CH:7]([CH3:9])[CH3:8])[C:3]([O:5][CH2:10][CH3:11])=[O:4]

参加物

6

反応物 3

HCID 962WaterHCID 6101p-Toluenesulfonic acidHCID 13633259(2S)-4-Methyl-2-sulfanylpentanoic acid

生成物 1

HCID 15673225HCID 15673225、化合物収率 3,077.9%

試薬・触媒・溶媒 2

HCID 702Ethanol溶媒HCID 6212Chloroform溶媒3 回

実験手順

A solution of 7.2 g (48.6 mmole) of (S)-2-mercapto-4 methylpentanoic acid [J. A. Yankeelov, Jr., K. F. Fok, and D. J. Carothers, J. Org Chem., 43, 1623 (1978)] and 219 mg of p-toluenesulfonic acid in 12 ml of absolute ethanol and 12 ml of CHCl3 was stirred under reflux with collection of liberated H2O in a Dean-Stark trap pre-filled with CHCl3. After 4 hours, the solution was cooled, diluted with an equal volume of CHCl3, and washed successively with H2O, saturated aqueous NaHCO3 solution, and H2O. The organic phase was dried over MgSO4, filtered, and concentrated to give 6.90 g (81%) of an oil, [α]20D -19.0° (c 2, ether), TLC in 9:1 hexane-ethyl acetate. The structure was verified by 200 MHz NMR (CDCl3).

後処理

  1. temperaturethe solution was cooled
  2. washwashed successively with H2O, saturated aqueous NaHCO3 solution, and H2O
  3. dry with materialThe organic phase was dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated

出典と根拠

ORDレコード
ord-abaf7bbc673746c0a9c8c17376792f69
出典データセット
uspto-grants-1992_05
特許番号
US05114925

関連ノート

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