L-Aspartic Acid → L-Phenylalanine, methyl ester
Reaction equation
N[C@H:2](C(O)=O)CC(O)=O.C(OC(Cl)=O)C1C=CC=CC=1.C(OC(N[C@H](C(O)=O)CC(O)=O)=O)C1C=CC=CC=1.[NH2:40][C@H:41]([C:49]([OH:51])=[O:50])[CH2:42][C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1>CO>[CH3:2][O:50][C:49](=[O:51])[C@H:41]([CH2:42][C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1)[NH2:40]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
A process for producing an addition compound of a dipeptide ester and an amino acid ester comprising reacting aspartic acid and benzyloxycarbonyl chloride in an aqueous solution in the presence of a base to prepare a solution containing N-benzyloxycarbonylaspartic acid, reacting separatedly phenylalanine with methanol in the presence of an acid to produce phenylalanine methyl ester adding a base therein to liberate the phenylalanine methyl ester, adding to admix an organic solvent capable of forming binary phases with water to extract the phenylalanine methyl ester in the organic solvent phase, separating the phases, adding an acidic aqueous solution into the organic solvent phase to admix and contact with to back-extract the phenylalanine methyl ester into the aqueous phase, separated the phases, admixing the aqueous phase with the above prepared aqueous solution containing N-benzyloxycarbonyl-aspartic acid, adding a proteolytic enzyme into the resulting mixture liquor under conditions under which no substantial deactivation of the enzyme occurrs, reacting N-benzyloxycarbonylaspartic acid with phenylalanine methyl ester to deposit an addition compound of N-benzyloxycarbonyl-α-L-aspartly-L-phenylalanine methyl ester and phenylalanine methyl ester and recovering the addition compound.
Workup
- customto prepare a solution
Sources & evidence
- ORD record
- ord-460487cad6e74883961aabae1034ebc7
- Source dataset
- uspto-grants-1985_06
- Patent number
- US04521514
Reaction notes
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