Acetic Anhydride → N-acetoacetyl-L-aspartyl-L-phenylalanine methyl ester

HRID 1583891

Reaktionsgleichung

Reaktionsgleichung von HRID 1583891
[C:1]([NH:7][C@@H:8]1[C:13](=[O:14])[O:12][C:10](=[O:11])[CH2:9]1)(=[O:6])[CH2:2][C:3]([CH3:5])=[O:4].C(OC(=O)C)(=O)C.[CH3:22][O:23][C:24](=[O:34])[C@H:25]([CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)[NH2:26]>>[CH3:22][O:23][C:24](=[O:34])[C@H:25]([CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)[NH:26][C:13](=[O:14])[C@H:8]([CH2:9][C:10](=[O:11])[OH:12])[NH:7][C:1](=[O:6])[CH2:2][C:3]([CH3:5])=[O:4]

Komponenten

4

Edukt 3

HCID 7918Acetic AnhydrideHCID 736234L-Phenylalanine, methyl esterHCID 13334674N-acetoacetyl-L-aspartic anhydride2×

Produkt 1

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

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-05d9f215620f4c3e98bb5531d5f20502
Quelldatensatz
uspto-grants-1985_11
Patentnummer
US04555362

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