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

反応式

[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]

参加物

反応物 3

HCID 7918Acetic Anhydride

HCID 736234L-Phenylalanine, methyl ester

HCID 13334674N-acetoacetyl-L-aspartic anhydride2 回

生成物 1

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

実験手順

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.

出典と根拠

ORDレコード: ord-5f2ff921844647c8986f33b874fd1567
出典データセット: uspto-grants-1984_04
DOI: 10.6084/m9.figshare.5104873.v1
特許番号: US04440677

反応ノート

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