Ethanol → Ethyl 5-oxo-L-prolinate

HRID 1731419

Reaktionsgleichung

Reaktionsgleichung von HRID 1731419
S(Cl)(Cl)=O.[NH2:5][C@H:6]([C:12]([OH:14])=[O:13])[CH2:7][CH2:8][C:9]([OH:11])=O.C(=O)([O-])[O-].[Na+].[Na+].[CH2:21](O)[CH3:22]>O>[NH:5]1[C:9](=[O:11])[CH2:8][CH2:7][C@H:6]1[C:12]([O:14][CH2:21][CH3:22])=[O:13]

Komponenten

6

Edukt 4

HCID 702EthanolHCID 10340Sodium CarbonateHCID 24386Thionyl ChlorideHCID 33032L-Glutamic Acid

Produkt 1

HCID 2724446Ethyl 5-oxo-L-prolinate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel2×

Reaktionsbedingungen

Temperatur
160 °C

Versuchsvorschrift

Thionyl chloride (217 ml) is slowly added to a stirred suspension of L-glutamic acid (417 g) in dry ethanol (1 L), and the mixture is refluxed for 5 hours. Ethanol is removed under vaccum to give a residue, which is dissolved in water (500 ml). The water solution is made alkaline with saturated sodium carbonate solution and extracted with chloroform (4×200 ml). The chloroform extract is dried (Na2SO4) and evaporated to give crude product (178 g). This material is heated (160° C.) under vaccum (10 mm Hg) for 3 hours. Subsequent distillation gives pure ethyl L-pyroglutamate (126.6 g; b.p. 126° C./0.07 mm Hg; [α]D =-2.15°±0.01 (H2O, c=17.8).

Aufarbeitung

  1. temperaturethe mixture is refluxed for 5 hours
  2. customEthanol is removed under vaccum
  3. customto give a residue, which
  4. extractionextracted with chloroform (4×200 ml)
  5. extractionThe chloroform extract
  6. dry with materialis dried (Na2SO4)
  7. customevaporated
  8. customto give crude product (178 g)
  9. distillationSubsequent distillation

Quellen und Nachweise

ORD-Eintrag
ord-b8a0e7cd4fcd4c7295dd45f5bcbb5ad9
Quelldatensatz
uspto-grants-1986_11
Patentnummer
US04621145

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