L-Phenylalanine → Aspartame

HRID 1464208Notes

Reaction equation

HRID 1464208 reaction equation
[CH3:1][O:2][C:3](=[O:13])[C@H:4]([CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[NH2:5].C([NH:16][C@@H:17]1[C:22](=[O:23])[O:21][C:19](=[O:20])[CH2:18]1)=O.N[C@H](C(O)=O)CC1C=CC=CC=1>C(O)(=O)C>[CH3:1][O:2][C:3](=[O:13])[C@H:4]([CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[NH:5][C:22](=[O:23])[C@H:17]([CH2:18][C:19](=[O:20])[OH:21])[NH2:16]

Participants

5

Reactant 3

HCID 6140L-PhenylalanineHCID 736234L-Phenylalanine, methyl esterHCID 11298025N-[(3S)-Tetrahydro-2,5-dioxo-3-furanyl]formamide

Product 1

HCID 134601Aspartame

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

In a known process which does not use L-phenylalanine methyl ester, N-formyl-L-aspartic anhydride is subjected to a condensation reaction with L-phenylalanine in acetic acid and then the formyl group is removed in the presence of an aqueous hydrogen halide solution. The reaction product is subsequently esterified by treating with water, alcohol and the aqueous hydrogen halide solution, and α-L-aspartyl-L-phenylalanine methyl ester is isolated in the form of its hydrogen halide salt (U.S. Pat. No. 3,933,781).

Workup

  1. customthe formyl group is removed in the presence of an aqueous hydrogen halide solution
  2. additionby treating with water, alcohol

Sources & evidence

ORD record
ord-49d9de241de1431abd6d8516eae85ff8
Source dataset
uspto-grants-1994_04
Patent number
US05302743

Reaction notes

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