D-Methionine → (2R)-2-Hydroxy-4-(methylthio)butanoic acid

HRID 2352049Notes

Reaction equation

HRID 2352049 reaction equation
N[C@@H:2]([C:7]([OH:9])=[O:8])[CH2:3][CH2:4][S:5][CH3:6].N([O-])=[O:11].[Na+]>OS(O)(=O)=O.O>[OH:11][C@H:2]([CH2:3][CH2:4][S:5][CH3:6])[C:7]([OH:9])=[O:8]

Participants

5

Reactant 2

HCID 84815D-MethionineHCID 23668193Sodium Nitrite

Product 1

HCID 9942187(2R)-2-Hydroxy-4-(methylthio)butanoic acidYield 10%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1118Sulfuric AcidSolvent

Procedure

D-Methionine (100 g, 0.67 mol) was dissolved in 600 ml of 10% H2SO4 and cooled to 0°-5° C. A solution of NaNO2 (58 g, 0.84 mol) in 100 ml of H2O, also chilled to 0°-5° C., was added dropwise over 1.5 hours, maintaining the temperature of the reaction mixture at 0° C. or less by means of an ice water bath. After stirring for 18 hours at room temperature, the mixture was extracted 9×200 ml ethyl acetate. The organic extracts were combined, dried over MgSO4, and stripped to yield 10.1 g of title product as oil; tlc Rf 0.15 (ethyl acetate), 0.08 (1:1 hexane:ethyl acetate).

Workup

  1. temperaturecooled to 0°-5° C
  2. additionwas added dropwise over 1.5 hours
  3. temperaturemaintaining the temperature of the reaction mixture at 0° C. or less by means of an ice water bath
  4. extractionthe mixture was extracted 9×200 ml ethyl acetate
  5. dry with materialdried over MgSO4

Sources & evidence

ORD record
ord-acfeff766a16411faa62bd51d24ffedd
Source dataset
uspto-grants-1989_10
Patent number
US04874877

Reaction notes

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