Reaktion #4464

ord-f01be8f761ca4562ae3496ae6ef3ae07

Reaktionsgleichung

C[C@H](N)C(=O)N1CCC[C@H]1C(=O)OC(C)(C)C
(S)-alanyl-(S)-proline-t-butylester
CCOC(=O)/C=C/C(=O)c1ccccc1
E-ethyl-3-benzoyl-acrylate
O=C(O)/C=C\C(=O)O
maleinic acid
→
CCOC(=O)[C@H](CC(=O)c1ccccc1)N[C@@H](C)C(=O)N1CCC[C@H]1C(=O)OC(C)(C)C.O=C(O)/C=C\C(=O)O
product
Ausbeute 60.0%
CCOC(=O)[C@H](CC(=O)c1ccccc1)N[C@@H](C)C(=O)N1CCC[C@H]1C(=O)OC(C)(C)C.O=C(O)/C=C\C(=O)O
N-[1(S)-ethoxycarbonyl-3-phenyl-3-oxo-propyl]-(S)-alanyl-(S)-proline-t-butyl-ester maleate
Ausbeute 60.0%

Edukte

C[C@H](N)C(=O)N1CCC[C@H]1C(=O)OC(C)(C)C
(S)-alanyl-(S)-proline-t-butylester
CCOC(=O)/C=C/C(=O)c1ccccc1
E-ethyl-3-benzoyl-acrylate
O=C(O)/C=C\C(=O)O
maleinic acid

Reagenzien

Keine

Lösungsmittel

c1ccccc1
benzene

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    workup.STIRRINGAfter one hour stirring at room temperature the solvent
  2. 2
    Sonstigeis evaporated off under reduced pressure
  3. 3
    workup.DISSOLUTIONthe residue is dissolved in 20 ml of ethyl acetate
  4. 4
    FiltrationThe precipitated crystals are filtered off after one hour standing
  5. 5
    Waschenwashed with 20 ml of ethyl acetate

Vorschrift

4.84 g (20 mmoles) of (S)-alanyl-(S)-proline-t-butylester are dissolved in 40 ml of dry benzene and 4.08 g (20 mmoles) of E-ethyl-3-benzoyl-acrylate are added at room temperature under stirring. After one hour stirring at room temperature the solvent is evaporated off under reduced pressure, the residue is dissolved in 20 ml of ethyl acetate and 2.32 g (20 mmoles) of maleinic acid are added. The precipitated crystals are filtered off after one hour standing and washed with 20 ml of ethyl acetate. 6.7 g (60%) of product are obtained with a melting point of 109°-110° C.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US04725617uspto-grants-1988_02