Reaktion #1668071

ord-28863a353b1e45869402690dfe406e62

Reaktionsgleichung

NC(=O)CC[C@H](NC(=O)OCc1ccccc1)C(=O)Oc1ccc([N+](=O)[O-])cc1
Z-Gln-ONP
COC(=O)[C@H](Cc1ccccc1)NC(=O)[C@@H](N)CC(N)=O
H-Asn-Phe-OCH3
Cl
hydrochloride
→
COC(=O)[C@H](Cc1ccccc1)NC(=O)[C@H](CC(N)=O)NC(=O)[C@H](CCC(N)=O)NC(=O)OCc1ccccc1
Z-Gln-Asn-Phe-OCH3

Edukte

NC(=O)CC[C@H](NC(=O)OCc1ccccc1)C(=O)Oc1ccc([N+](=O)[O-])cc1
Z-Gln-ONP
COC(=O)[C@H](Cc1ccccc1)NC(=O)[C@@H](N)CC(N)=O
H-Asn-Phe-OCH3
Cl
hydrochloride

Reagenzien

Keine

Lösungsmittel

CN(C)C=O
dimethylformamide
CN(C)C=O
dimethylformamide
CCN(CC)CC
triethylamine

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    workup.ADDITIONare added slowly
  2. 2
    SonstigeAfter a reaction period of 24 hours at room temperature
  3. 3
    Filtrationthe batch is filtered
  4. 4
    Waschenthe residue washed with dimethylformamide
  5. 5
    SonstigeThe resulting Z-Gln-Asn-Phe-OMe can be recrystallized from much hot dimethylformamide
  6. 6
    Sonstige[α]20D = + 11° (c = 0.94 in hexamethylphosphoric acid triamide)

Vorschrift

14.5 of Z-Gln-ONP and 10.8 g of H-Asn-Phe-OCH3, hydrochloride (Ann. 688, 259 [1965]) are dissolved together in 100 ml of dimethylformamide and to the solution 4.55 ml of triethylamine are added slowly. A thick paste forms which is diluted with 50 ml of dimethylformamide. After a reaction period of 24 hours at room temperature, the batch is filtered and the residue washed with dimethylformamide. The resulting Z-Gln-Asn-Phe-OMe can be recrystallized from much hot dimethylformamide. Melting point, 261°-265°C (decomp.). [α]20D = + 11° (c = 0.94 in hexamethylphosphoric acid triamide).

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US03934008uspto-grants-1976_01