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

HRID 868367Notes

Reaction equation

HRID 868367 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].Cl.[CH:23](N[C@@H]1C(=O)OC(=O)C1)=[O:24].N[C@H](C(O)=O)CC1C=CC=CC=1>O>[CH:23]([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:24]

Participants

6

Reactant 4

HCID 313Hydrochloric Acid2×HCID 6140L-PhenylalanineHCID 134601Aspartame2×HCID 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

This invention relates to a preparation process of α-L-aspartyl-L-phenylalanine methyl ester or its hydrochloride. More specifically, this invention provides a process for preparing α-L-aspartyl-L-phenylalanine methyl ester or its hydrochloride which process comprises: condensating N-formyl-L-aspartic acid anhydride and L-phenylalanine in water at a pH in the range of 7-12 to form N-formyl-α-L-aspartyl-L-phenylalanine; acidifying the reaction mixture with hydrochloric acid in the presence of methanol without isolating the N-formyl-α-L-aspartyl-L-phenylalanine so as to bring it into contact with hydrochloric acid in the presence of methanol for reaction and thereby to precipitate α-L-aspartyl-L-phenylalanine methyl ester hydrochloride; separating the α-L-aspartyl-L-phenylalanine methyl ester hydrochloride; and neutralizing said hydrochloride as required. Further, this invention provides another process for preparing α-L-aspartyl-L-phenylalanine methyl ester or its hydrochloride which process comprises: condensating N-formyl-L-aspartic acid anhydride and L-phenylalanine in water containing methanol in an amount of 6 moles or less per mol of the L-phenylalanine at a pH in the range of 7-12 to form N-formyl-α-L-aspartyl-L-phenylalanine; acidifying the reaction mixture with hydrochloric acid without isolating the N-formyl-α-L-aspartyl-L-phenylalanine so as to bring it into contact with hydrochloric acid in the presence of methanol for reaction and thereby to precipitate α-L-aspartyl-L-phenylalanine methyl ester hydrochloride; separating the α-L-aspartyl-L-phenylalanine methyl ester hydrochloride; and neutralizing said hydrochloride as required.

Workup

  1. customMore specifically, this invention provides a process

Sources & evidence

ORD record
ord-b42d94dc3d7442d49553b369f49d4b76
Source dataset
uspto-grants-1988_10
Patent number
US04778916

Reaction notes

Loading…