Water → HCID 15673225, compound

HRID 1196458

Reaction equation

HRID 1196458 reaction equation
[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]

Participants

6

Reactant 3

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

Product 1

HCID 15673225HCID 15673225, compoundYield 3,077.9%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6212ChloroformSolvent3×

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-abaf7bbc673746c0a9c8c17376792f69
Source dataset
uspto-grants-1992_05
Patent number
US05114925

Linked notes

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