Water → HCID 15673225, 화합물

HRID 1196458

반응식

HRID 1196458 반응식
[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]

참가 물질

6

반응물 3

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

생성물 1

HCID 15673225HCID 15673225, 화합물수율 3,077.9%

시약·촉매·용매 2

HCID 702Ethanol용매HCID 6212Chloroform용매3회

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-abaf7bbc673746c0a9c8c17376792f69
출처 데이터셋
uspto-grants-1992_05
특허 번호
US05114925

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