Reaktion #451397

ord-080734b284b144d79f895f368eae62e5

Reaktionsgleichung

N[C@@H](CCC(=O)O)C(=O)O
L-glutamic acid
CCOC(=O)c1cccc2c1C(=O)NC2=O
Carboethoxy phthalimide
Cl
HCl
→
O=C(O)CC[C@@H](C(=O)O)N1C(=O)c2ccccc2C1=O
N,N-phthaloylglutamic acid

Edukte

N[C@@H](CCC(=O)O)C(=O)O
L-glutamic acid
CCOC(=O)c1cccc2c1C(=O)NC2=O
Carboethoxy phthalimide
Cl
HCl

Reagenzien

Keine

Lösungsmittel

O=C([O-])[O-].[Na+].[Na+]
Na2CO3
O
water

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    Sonstigereacted at 350° C. for 30-40 minutes
  2. 2
    Sonstigeto stand at 0° C
  3. 3
    FiltrationThe resulting precipitate was filtered
  4. 4
    Sonstigerecrystallized from water

Vorschrift

In a solution of Na2CO3 (51.5 g) in water (350 ml) at 5° C. was dissolved L-glutamic acid (29.4 g). Carboethoxy phthalimide (59.6 g) was added to the solution and suspended therein and thereafter reacted at 350° C. for 30-40 minutes. Then the solution was freed from insoluble matter, adjusted to pH 2.5 with 6N-HCl, and allowed to stand at 0° C. The resulting precipitate was filtered, and recrystallized from water to give N,N-phthaloylglutamic acid, yield 35.7 g, 64.4%; specific rotation [α]D25 =-48.6° (C=1, dioxane).

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US04604451uspto-grants-1986_08