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

HRID 845864Notes

Reaction equation

HRID 845864 reaction equation
C[O:2][C:3](=[O:21])[C@H:4]([CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[NH:5][C:6](=[O:13])[C@H:7]([CH2:9][C:10](=[O:12])[OH:11])[NH2:8].[CH:22](N[C@@H]1C(=O)OC(=O)C1)=[O:23].N[C@H](C(O)=O)CC1C=CC=CC=1>O>[CH:22]([NH:8][C@H:7]([C:6]([NH:5][C@H:4]([C:3]([OH:2])=[O:21])[CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[O:13])[CH2:9][C:10](=[O:12])[OH:11])=[O:23]

Participants

5

Reactant 3

HCID 6140L-PhenylalanineHCID 134601AspartameHCID 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 962WaterSolvent

Procedure

A process for preparing an α-L-aspartyl-L-phenylalanine methyl ester which comprises the steps of reacting formyl-L-aspartic anhydride with L-phenylalanine in the presence of water at a high pH, to produce formyl-α-L-aspartyl-L-phenylalanine; removing the formyl group from the formyl-α-L-aspartyl-L-phenylalanine and esterifying the resultant compound with methanol and hydrogen chloride to produce the hydrogen chloride salt of α-L-aspartyl-L-phenylalanine methyl ester; neutralizing the hydrogen chloride salt of α-L-aspartyl-L-phenylalanine methyl ester; and filtering the neutralized solution to produce α-L-aspartyl-L-phenylalanine methyl ester.

Sources & evidence

ORD record
ord-8794dc2af3a447adb4623336d8fe0c73
Source dataset
uspto-grants-1988_07
Patent number
US04760164

Reaction notes

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