L-Phenylalanine → L-Aspartyl-L-phenylalanine

HRID 653547Notes

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

Participants

Reactant 2

HCID 6140L-Phenylalanine

HCID 134601Aspartame

Product 1

HCID 93078L-Aspartyl-L-phenylalanine

Procedure

A regioselective process for the preparation of α-L-aspartyl-L-phenylalanine methyl ester is disclosed. A controlled aqueous coupling reaction between β-methyl-L-aspartate-N-carboxyanhydride and L-phenylalanine produces the aspartyl methyl ester of α-L-aspartyl-L-phenylalanine which is subsequently hydrolyzed and selectively esterified without isolation. The hydrochloride salt of α-L-aspartyl-L-phenylalanine methyl ester, which is selectively precipitated from the esterification mixture, can be neutralized to α-L-aspartyl-L-phenylalanine methyl ester.

Sources & evidence

ORD record: ord-b0d90e636ed441648e1d8344b289d6e1
Source dataset: uspto-grants-1987_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04677220

Reaction notes

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