Hydrochloric Acid → Aspartame

HRID 1580547Notes

Reaction equation

HRID 1580547 reaction equation
C([NH:3][C@H:4]([C:9]([NH:11][C@H:12]([C:20]([OH:22])=[O:21])[CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[O:10])[CH2:5][C:6](=[O:8])[OH:7])=O.Cl.[CH3:24]O>>[CH3:24][O:22][C:20](=[O:21])[C@H:12]([CH2:13][C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1)[NH:11][C:9](=[O:10])[C@H:4]([CH2:5][C:6](=[O:8])[OH:7])[NH2:3]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 887MethanolHCID 92472N-(N-Formyl-L-alpha-aspartyl)-3-phenyl-L-alanine

Product 1

HCID 134601Aspartame

Procedure

A process comprising reacting N-formyl-aspartic anhydride with l-phenylalanine in glacial acetic acid to form N-formyl-α-L-aspartyl-L-phenylalanine, removing the formyl group from N-formyl-α-L-aspartyl-L-phenylalanine by hydrolysis with an aqueous solution of hydrogen chloride and esterifying the resulting α-L-aspartyl-L-phenylalanine with methanol in the presence of hydrogen chloride to form α-L-aspartyl-L-phenylalanine methyl ester and recovering the α-L-asparatyl-L-phenylalanine methyl ester.

Workup

  1. customremoving the formyl group from N-formyl-α-L-aspartyl-L-phenylalanine
  2. customby hydrolysis with an aqueous solution of hydrogen chloride

Sources & evidence

ORD record
ord-b29b134a18774719ad7e3e255f03689a
Source dataset
uspto-grants-1976_01
Patent number
US03933781

Reaction notes

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