Diketene → N-acetoacetyl-L-aspartyl-L-phenylalanine methyl ester

HRID 325273

Reaktionsgleichung

Reaktionsgleichung von HRID 325273
[CH2:1]=[C:2]1[O:6][C:4](=[O:5])[CH2:3]1.[CH3:7][O:8][C:9](=[O:27])[C@H:10]([CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[NH:11][C:12](=[O:19])[C@H:13]([CH2:15][C:16](=[O:18])[OH:17])[NH2:14]>O1CCCC1>[CH3:7][O:8][C:9](=[O:27])[C@H:10]([CH2:20][C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1)[NH:11][C:12](=[O:19])[C@H:13]([CH2:15][C:16](=[O:17])[OH:18])[NH:14][C:4](=[O:5])[CH2:3][C:2]([CH3:1])=[O:6]

Komponenten

4

Edukt 2

HCID 12661Diketene2×HCID 134601Aspartame

Produkt 1

HCID 13334676N-acetoacetyl-L-aspartyl-L-phenylalanine methyl ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

4.5 parts of diketene were added dropwise to a stirred suspension of 14.7 parts α-L-aspartyl-L-phenylalanine methyl ester in 400 parts by volume of tetrahydrofuran and stirred for 20 hours at ambient temperatures. An additional 4.2 parts of diketene was added. After 18 hours, the solvent was removed under vacuum and the residue was purified by chromotography on silica gel to give N-acetoacetyl-α-L-aspartyl-L-phenylalanine methyl ester, mp. 118.5°-121° C. which eluted in a 10:90:0.1 ethanol:methylene chloride:acetic acid mixture.

Aufarbeitung

  1. waitAfter 18 hours
  2. customthe solvent was removed under vacuum
  3. customthe residue was purified by chromotography on silica gel

Quellen und Nachweise

ORD-Eintrag
ord-b2881bece4c24faa94fa579e10d8d880
Quelldatensatz
uspto-grants-1984_04
Patentnummer
US04440677

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