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

HRID 868712Notes

Reaction equation

HRID 868712 reaction equation
COC(=O)CC1C(=O)NC(CC2C=CC=CC=2)C(=O)N1.[CH:21]([NH:23][C@@H:24]1[C:29](=[O:30])[O:28][C:26](=[O:27])[CH2:25]1)=[O:22].[NH2:31][C@H:32]([C:40]([OH:42])=[O:41])[CH2:33][C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1>>[CH:21]([NH:23][C@H:24]([C:29]([NH:31][C@H:32]([C:40]([OH:42])=[O:41])[CH2:33][C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)=[O:30])[CH2:25][C:26](=[O:27])[OH:28])=[O:22]

Participants

4

Reactant 3

HCID 6140L-PhenylalanineHCID 11298025N-[(3S)-Tetrahydro-2,5-dioxo-3-furanyl]formamideHCID 138837735-Benzyl-3,6-dioxo-2-piperazine acetic acid methyl ester

Product 1

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

Procedure

5-benzyl-3,6-dioxo-2-piperazine acetic acid methyl ester can be prepared by condensating N-formyl-L-aspartic acid anhydride with L-phenylalanine to form N-formyl-α-L-aspartyl-L-phenylalanine, de-formylating and diesterifying the N-formyl-α-L-aspartyl-L-phenylalanine in methanol in the presence of an acid to produce α-L-aspartyl-L-phenylalanine dimethyl ester, and treating said diester, for example, in a mixed solvent of water and methanol under neutral or weakly alkaline conditions;

Sources & evidence

ORD record
ord-e92b752d32164dcaa3f159629164949c
Source dataset
uspto-grants-1988_10
Patent number
US04780561

Reaction notes

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