L-Aspartic Acid → N-acetoacetylaspartic acid

HRID 325264

Reaktionsgleichung

COC(=O)[C@H](CC1C=CC=CC=1)NC(=O)[C@H](CC(=O)O)N.[NH2:22][C@H:23]([C:28]([OH:30])=[O:29])[CH2:24][C:25]([OH:27])=[O:26].[CH2:31]=[C:32]1[O:36][C:34](=[O:35])[CH2:33]1>>[C:34]([NH:22][C@H:23]([C:28]([OH:30])=[O:29])[CH2:24][C:25]([OH:27])=[O:26])(=[O:35])[CH2:33][C:32]([CH3:31])=[O:36]

Komponenten

Edukt 3

HCID 5960L-Aspartic Acid

HCID 12661Diketene

HCID 134601Aspartame

Produkt 1

HCID 13334672N-acetoacetylaspartic acid

Versuchsvorschrift

This invention encompasses a method and intermediates for preparing a commercial sweetening agent, α-L-aspartyl-L-phenylalanine methyl ester. The process involves reacting L-aspartic acid with diketene to form N-acetoacetyl-L-aspartic acid which is converted to N-acetoacetyl-L-aspartic anhydride by reaction with acetic anhydride. N-acetoacetyl-L-aspartic anhydride is reacted with L-phenylalanine methyl ester to provide N-acetoacetyl-α-L-aspartyl-L-phenylalanine methyl ester which is converted to α-L-aspartyl-L-phenylalanine methyl ester by reaction with hydroxylamine hydrochloride.

Quellen und Nachweise

ORD-Eintrag: ord-e3ace9b8c72e403c8b3f7e990e0b28f7
Quelldatensatz: uspto-grants-1984_04
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US04440677

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