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

HRID 868368Notes

Reaction equation

HRID 868368 reaction equation
Cl.C[O:3][C:4](=[O:22])[C@H:5]([CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[NH:6][C:7](=[O:14])[C@H:8]([CH2:10][C:11](=[O:13])[OH:12])[NH2:9].[CH:23](N[C@@H]1C(=O)OC(=O)C1)=[O:24].N[C@H](C(O)=O)CC1C=CC=CC=1>O.CO>[CH:23]([NH:9][C@H:8]([C:7]([NH:6][C@H:5]([C:4]([OH:3])=[O:22])[CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[O:14])[CH2:10][C:11](=[O:13])[OH:12])=[O:24]

Participants

7

Reactant 4

HCID 313Hydrochloric Acid2×HCID 6140L-Phenylalanine2×HCID 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 2

HCID 887MethanolSolvent2×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. customfor reaction
  2. customto precipitate α-L-aspartyl-L-phenylalanine methyl ester hydrochloride
  3. customseparating the α-L-aspartyl-L-phenylalanine methyl ester hydrochloride
  4. customFurther, this invention provides another process

Sources & evidence

ORD record
ord-33ccb3d9fec14fa2917f80a66bf98e55
Source dataset
uspto-grants-1988_10
Patent number
US04778916

Reaction notes

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