Hydrochloric Acid → Hydrochloric Acid

HRID 868366Notes

Reaction equation

HRID 868366 reaction equation
[CH3:1][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].[ClH:22].[CH:23]([NH:25][C@@H:26]1[C:31](=[O:32])[O:30][C:28](=[O:29])[CH2:27]1)=[O:24].[NH2:33][C@H:34]([C:42]([OH:44])=[O:43])[CH2:35][C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1>O.CO>[CH3:1][O:2][C:3](=[O:21])[C@H:4]([CH2:14][C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1)[NH:5][C:6](=[O:13])[C@H:7]([CH2:9][C:10](=[O:11])[OH:12])[NH2:8].[ClH:22].[CH:23]([NH:25][C@H:26]([C:31]([NH:33][C@H:34]([C:42]([OH:44])=[O:43])[CH2:35][C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1)=[O:32])[CH2:27][C:28](=[O:29])[OH:30])=[O:24]

Participants

9

Reactant 4

HCID 313Hydrochloric AcidHCID 6140L-PhenylalanineHCID 134601AspartameHCID 11298025N-[(3S)-Tetrahydro-2,5-dioxo-3-furanyl]formamide

Product 3

HCID 313Hydrochloric AcidHCID 92472N-(N-Formyl-L-alpha-aspartyl)-3-phenyl-L-alanineHCID 134601Aspartame

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent2×

Procedure

The present invention relates to a process for preparing α-L-aspartyl-L-phenylalanine methyl ester or its hydrochloride. α-L-aspartyl-L-phenylalanine methyl ester or its hydrochloride is prepared by a process comprising: condensating N-formyl-L-aspartic acid anhydride and L-phenylalanine in water or in water containing methanol at a pH in the range of 7-12 to form N-formyl-α-L-aspartyl-L-phenylalanine; acidifying the reaction mixture successively 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 deposit α-L-aspartyl-L-phenylalanine methyl ester hydrochloride; separating the α-L-aspartyl-L-phenylalanine methyl ester hydrochloride; and neutralizing said hydrochloride as required.

Sources & evidence

ORD record
ord-539e94da77a349f2973308e2a06070ff
Source dataset
uspto-grants-1988_10
Patent number
US04778916

Reaction notes

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