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Methane → 2-(Acetyloxy)-4-(methylsulfanyl)butanoic acid

HRID 1754042
Notes
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Reaction equation

HRID 1754042 reaction equation
[CH3:1][S:2][CH2:3][CH2:4][CH:5]([OH:9])[C:6]([OH:8])=[O:7].C.C(N(CC)CC)C.[C:18](Cl)(=[O:20])[CH3:19]>>[C:18]([O:9][CH:5]([CH2:4][CH2:3][S:2][CH3:1])[C:6]([OH:8])=[O:7])(=[O:20])[CH3:19]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 4

HCID 297MethaneHCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 11427alpha-Hydroxy-gamma-methylmercaptobutyric acid

Product 1

HCID 30747282-(Acetyloxy)-4-(methylsulfanyl)butanoic acidYield 63.1%

Conditions

Temperature
0 °C

Procedure

To a solution of 2-hydroxy-4-(methylthio)butanoic acid (50.74 g, 337.8 mmol, obtained by stirring Alimet over activated charcoal, filtering and concentrating in a rotovap) in dichloromethane (1 L) was added triethylamine (93 mL, 667.3 mmol) and the resulting mixture was cooled to 0° C. To the cooled mixture was added acetyl chloride (26 mL, 365.6 mmol) dropwise. The ice bath was removed and the reaction was allowed to warm to room temperature overnight. The reaction was washed with 1N HCl (2×300 mL), and brine (1×300 mL), dried over magnesium sulfate, filtered and evaporated to give an amber oil (59.82 g, 63.1%). m/z 193 (MH+).

Workup

  1. filtrationfiltering
  2. concentrationconcentrating in a rotovap) in dichloromethane (1 L)
  3. customThe ice bath was removed
  4. temperatureto warm to room temperature overnight
  5. washThe reaction was washed with 1N HCl (2×300 mL), and brine (1×300 mL)
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. customevaporated

Sources & evidence

ORD record
ord-8a45b48979be4167b65dfe0a1edf247a
Source dataset
uspto-grants-2015_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09169203B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes