Benzyl chloroformate → Z-Glu(ome)-OH

HRID 369778

Reaktionsgleichung

Reaktionsgleichung von HRID 369778
[CH3:1][O:2][C:3]([CH2:5][CH2:6][C@H:7]([NH2:11])[C:8]([OH:10])=[O:9])=[O:4].C([O-])(O)=O.[Na+].Cl[C:18]([O:20][CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)=[O:19]>O>[CH2:21]([O:20][C:18]([NH:11][C@H:7]([C:8]([OH:10])=[O:9])[CH2:6][CH2:5][C:3]([O:2][CH3:1])=[O:4])=[O:19])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Komponenten

5

Edukt 3

HCID 10387Benzyl chloroformateHCID 686625-Methyl hydrogen L-glutamateHCID 516892Sodium Bicarbonate

Produkt 1

HCID 6350584Z-Glu(ome)-OHAusbeute 92 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

To a 1 L 3-necked flask equipped with a thermometer and a magnetic stirrer were added 4.90 g of L-glutamic acid γ-methyl ester (Sigma) and 200 mL of water. The solution was heated to 60° C., treated with 6.40 g of NaHCO3 followed by 5.20 mL of benzyl chloroformate (Aldrich) and allowed to cool to RT with vigorous stirring. After 4 h the reaction mixture was extracted with ethyl ether (4×100 mL) and the ether extracts were discarded. The aqueous solution was acidified to a congo red endpoint by addition of concentrated HCl. An oily emulsion resulted which was extracted with CH2Cl2 (4×60 mL). The combined organic extracts were washed with 0.05 N aqueous HCl (2×60 mL), dried over anhydrous Na2SO4 and concentrated in vacuo to afford 8.23 g (92%) of N-((benzyloxy)carbonyl)-5-O-methyl-L-glutamic acid as a white crystalline solid, m.p. 61-63° C.

Aufarbeitung

  1. customTo a 1 L 3-necked flask equipped with a thermometer and a magnetic stirrer
  2. temperatureto cool to RT with vigorous stirring
  3. extractionAfter 4 h the reaction mixture was extracted with ethyl ether (4×100 mL)
  4. additionThe aqueous solution was acidified to a congo red endpoint by addition of concentrated HCl
  5. customAn oily emulsion resulted which
  6. extractionwas extracted with CH2Cl2 (4×60 mL)
  7. washThe combined organic extracts were washed with 0.05 N aqueous HCl (2×60 mL)
  8. dry with materialdried over anhydrous Na2SO4
  9. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-27f45152739b4d08ae37ee06c3464432
Quelldatensatz
uspto-grants-2000_10
Patentnummer
US06140100

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