L-Phenylalanine → N-(N-Formyl-L-alpha-aspartyl)-3-phenyl-L-alanine

HRID 1580546Notes

Reaction equation

HRID 1580546 reaction equation
[CH:1]([NH:3][C@@H:4]1[C:9](=[O:10])[O:8][C:6](=[O:7])[CH2:5]1)=[O:2].[NH2:11][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>C(O)(=O)C>[CH:1]([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:7])[OH:8])=[O:2]

Participants

4

Reactant 2

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

Product 1

HCID 92472N-(N-Formyl-L-alpha-aspartyl)-3-phenyl-L-alanine

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

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.

Sources & evidence

ORD record
ord-8f52686a9f5c4721801232f87b8c6c50
Source dataset
uspto-grants-1976_01
Patent number
US03933781

Reaction notes

Loading…