Phosgene → L-Glutamic acid, 5-(phenylmethyl) ester

HRID 874081

Reaktionsgleichung

Reaktionsgleichung von HRID 874081
O[NH:2][C@H:3]([C:16](N)=[O:17])[CH2:4][CH2:5][C:6](=[O:15])[O:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.C(Cl)(Cl)=[O:20]>C1COCC1>[NH2:2][C@H:3]([C:16]([OH:17])=[O:20])[CH2:4][CH2:5][C:6](=[O:15])[O:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Komponenten

4

Edukt 2

HCID 6371PhosgeneHCID 131732571HO-Glu(Bzl)-NH2

Produkt 1

HCID 122337L-Glutamic acid, 5-(phenylmethyl) esterAusbeute 99,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

HO-Glu(Bzl)-NH2 (30.0 g, 126.0 mmol) was suspended in 300 mL of anhydrous THF and heated to 50° C. Phosgene (20% in toluene) (81.3 mL, 164.6 mmol) was added to the amino acid suspension by syringe, and the amino acid dissolved over the course of approx. 30 minutes, forming a clear solution. The solution was concentrated by rotory evaporation, dissolved in ˜150 mL of anhydrous THF, and transferred to an Erlenmeyer flask. Hexane was added and the product was allowed to crystallize overnight. The NCA was isolated by filtration and dried in vacuo. 29.8 g (90% yield) of Glu(Bzl) NCA was isolated as a white, crystalline solid. 1H NMR (CDCl3) δ 7.36 (5H), 6.22 (1H), 5.14 (2H), 4.35 (1H), 2.61 (2H), 2.29 (1H), 2.14 (1H) ppm.

Aufarbeitung

  1. customforming a clear solution
  2. concentrationThe solution was concentrated by rotory evaporation
  3. dissolutiondissolved in ˜150 mL of anhydrous THF
  4. additionHexane was added
  5. customto crystallize overnight
  6. customThe NCA was isolated by filtration
  7. customdried in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-7b8561a1c8dd467aa7304fb2998c6784
Quelldatensatz
uspto-grants-2015_03
Patentnummer
US08980326B2

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