Water → (R)-2-Acetoxy-4-(methylthio)butyric Acid

HRID 1031784

Reaktionsgleichung

Reaktionsgleichung von HRID 1031784
N[C@@H:2]([C:7]([OH:9])=[O:8])[CH2:3][CH2:4][S:5][CH3:6].N([O-])=O.[Na+].O.[C:15]([O:18]CC)(=[O:17])[CH3:16]>C(O)(=O)C>[C:15]([O:18][C@H:2]([CH2:3][CH2:4][S:5][CH3:6])[C:7]([OH:9])=[O:8])(=[O:17])[CH3:16]

Komponenten

6

Edukt 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 84815D-MethionineHCID 23668193Sodium Nitrite

Produkt 1

HCID 10954386(R)-2-Acetoxy-4-(methylthio)butyric Acid

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 176Acetic AcidLösungsmittel

Versuchsvorschrift

D-Methionine (14.9 g, 0.10 mol) was stirred in 300 ml of acetic acid. Sodium nitrite (13.8 g, 0.2 mol) was added portionwise over 45 minutes while maintaining the temperature in the range 20°-30° C. After stirring for an additional 90 minutes at room temperature, the resulting yellow solution was stripped in vacuo to solids which were distributed between 300 ml each of water and ethyl acetate. The organic layer was separated, washed with saturated NaCl, dried over MgSO4 and stripped to yield 7.0 g of title product as a yellow oil, used directly in the next step; tlc Rf 0.08 (3:1 hexane:ethyl acetate).

Aufarbeitung

  1. temperaturewhile maintaining the temperature in the range 20°-30° C
  2. customThe organic layer was separated
  3. washwashed with saturated NaCl
  4. dry with materialdried over MgSO4

Quellen und Nachweise

ORD-Eintrag
ord-1f6a28fcd55a4c98a474bc5626e59543
Quelldatensatz
uspto-grants-1990_09
Patentnummer
US04954647

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