反応 #412447

ord-5f2ff921844647c8986f33b874fd1567

反応方程式

CC(=O)CC(=O)N[C@H]1CC(=O)OC1=O
N-acetoacetyl-L-aspartic anhydride
CC(=O)OC(C)=O
acetic anhydride
CC(=O)CC(=O)N[C@H]1CC(=O)OC1=O
N-acetoacetyl-L-aspartic anhydride
COC(=O)[C@@H](N)Cc1ccccc1
L-phenylalanine methyl ester
→
COC(=O)[C@H](Cc1ccccc1)NC(=O)[C@H](CC(=O)O)NC(=O)CC(C)=O
N-acetoacetyl-α-L-aspartyl-L-phenylalanine methyl ester

反応物

CC(=O)CC(=O)N[C@H]1CC(=O)OC1=O
N-acetoacetyl-L-aspartic anhydride
CC(=O)OC(C)=O
acetic anhydride
CC(=O)CC(=O)N[C@H]1CC(=O)OC1=O
N-acetoacetyl-L-aspartic anhydride
COC(=O)[C@@H](N)Cc1ccccc1
L-phenylalanine methyl ester

試薬

なし

反応条件

詳細条件
See reaction.notes.procedure_details.

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

DOI: 10.6084/m9.figshare.5104873.v1特許: US04440677uspto-grants-1984_04