Potassium ethanethioate → (S)-2-(Acetylthio)-4,4-dimethylpentanoic acid

HRID 52809Notes

Reaction equation

HRID 52809 reaction equation
[C:1]([O-:4])(=[S:3])[CH3:2].[K+].Br[C@H:7]([CH2:11][C:12]([CH3:15])([CH3:14])[CH3:13])[C:8]([OH:10])=[O:9]>C(#N)C>[C:1]([S:3][C@@H:7]([CH2:11][C:12]([CH3:15])([CH3:14])[CH3:13])[C:8]([OH:10])=[O:9])(=[O:4])[CH3:2]

Participants

4

Reactant 2

HCID 23670855Potassium ethanethioateHCID 53849807HCID 53849807, compound

Product 1

HCID 53887840(S)-2-(Acetylthio)-4,4-dimethylpentanoic acid

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

A slurry of potassium thioacetate (750 mg, 6.58 mmol) and acetonitrile (10 ml, molecular sieves dried) was cooled to 0° C. and treated with a solution of (R)-2-bromo-4,4-dimethylpentanoic acid from part (a) in acetonitrile (2 ml) over 5 minutes. The reaction mixture was allowed to warm to room temperature and stirred for 2.5 hours. The slurry was filtered. The filtrate was concentrated in vacuo. The residue was diluted in ether (50 ml), washed with two portions of 5% aqueous sodium thiosulfate (50 ml) and brine (25 ml), dried (magnesium sulfate), and concentrated in vacuo. The pale yellow oil was purified by flash chromatography (Merck silica gel, 12×3 cm., 10% methanol/methylene chloride) affording 575 mg of title product as a pale yellow oil.

Workup

  1. filtrationThe slurry was filtered
  2. concentrationThe filtrate was concentrated in vacuo
  3. additionThe residue was diluted in ether (50 ml)
  4. washwashed with two portions of 5% aqueous sodium thiosulfate (50 ml) and brine (25 ml)
  5. dry with materialdried (magnesium sulfate)
  6. concentrationconcentrated in vacuo
  7. customThe pale yellow oil was purified by flash chromatography (Merck silica gel, 12×3 cm., 10% methanol/methylene chloride)

Sources & evidence

ORD record
ord-2b57d1dc57fe46baba24008f1f75b5d9
Source dataset
uspto-grants-1997_04
Patent number
US05616775

Reaction notes

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