L-Aspartic Acid → N-(1-methylcyclobutyloxycarbonyl) aspartic acid dimethyl ester

HRID 1605179Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1605179
COC(=O)[C@H](CC1C=CC=CC=1)NC(=O)[C@H](CC(=O)O)N.[CH3:22][C:23]1([O:27][C:28](N[C@@H]2C(=O)OC(=O)C2)=[O:29])[CH2:26][CH2:25][CH2:24]1.Cl.COC(=O)[C@H](CC1C=CC=CC=1)N.N[C@H](C(O)=O)CC(O)=O.[CH3:61][O:62][C:63](=[O:71])[C@H:64]([CH2:66][C:67]([O:69][CH3:70])=[O:68])[NH2:65].ClC([O-])=O.ClC(OC1(C)CCC1)=O>C(Cl)(Cl)Cl.C(N(CC)CC)C>[CH3:61][O:62][C:63](=[O:71])[C@H:64]([CH2:66][C:67]([O:69][CH3:70])=[O:68])[NH:65][C:28]([O:27][C:23]1([CH3:22])[CH2:26][CH2:25][CH2:24]1)=[O:29]

Komponenten

10

Edukt 7

HCID 5960L-Aspartic Acid2×HCID 75736Methyl L-phenylalaninate hydrochlorideHCID 1112071,4-Dimethyl L-aspartate2×HCID 134601AspartameHCID 21226386CarbonochloridateHCID 215491141-Methylcyclobutyl ChloroformateHCID 54330780N-(1-Methylcyclobutyloxycarbonyl)-Aspartic Anhydride

Produkt 1

HCID 54510473N-(1-methylcyclobutyloxycarbonyl) aspartic acid dimethyl ester

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6212ChloroformLösungsmittel2×HCID 8471TriethylamineLösungsmittel

Versuchsvorschrift

An example of the use of the novel N-protected-α-amino acid compounds of this invention in peptide synthesis is the preparation of α-aspartyl-phenylalanine methyl ester, a known sweetening agent. The dipeptide is conveniently prepared by coupling N-(1-methylcyclobutyloxycarbonyl) aspartic anhydride with phenylalanine methyl ester hydrochloride. Introduction of the N-(1-methylcyclobutyloxycarbonyl blocking group into aspartic acid is accomplished by reacting 1-methylcyclobutylchloroformate with aspartic acid dimethyl ester in accordance with the process of this invention. Equimolar quantities of the chloroformate and aspartic acid dimethyl ester are reacted in chloroform at 0°C. at pH 8. Reaction is carried out by portion-wise addition of 1-methylcyclobutyl chloroformate to the aspartic acid suspended in chloroform. Triethylamine is added to the reaction during the addition to maintain pH 8. After allowing the reaction to run to completion at room temperature, the reaction mixture is treated according to the procedure outlined above to afford the N-(1-methylcyclobutyloxycarbonyl) aspartic acid dimethyl ester. The free acid is obtained by saponifying the ester in a basic aqueous methanol solution. After acidifying the reaction mixture with sulfuric acid, the N-(1-methylcyclobutyloxycarbonyl) aspartic acid is isolated by extraction.

Aufarbeitung

  1. customReaction
  2. temperatureto maintain pH 8
  3. customthe reaction
  4. customto run to completion at room temperature
  5. additionthe reaction mixture is treated

Quellen und Nachweise

ORD-Eintrag
ord-b51c28ba7a6747918b78e74685af91d4
Quelldatensatz
uspto-grants-1976_04
Patentnummer
US03948971

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