L-Aspartic Acid → L-Phenylalanine, methyl ester

HRID 1248002Notes

Reaction equation

HRID 1248002 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

6

Reactant 4

HCID 5960L-Aspartic AcidHCID 6140L-PhenylalanineHCID 10387Benzyl chloroformateHCID 2723942N-(Benzyloxycarbonyl)aspartic acid

Product 1

HCID 736234L-Phenylalanine, methyl ester

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

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-benzyloxycarbonyl aspartic acid, reacting separatedly phenylalanine with methanol in the presence of an acid to produce phenylalanine methyl ester, substituting excess methanol with water to convert it to an aqueous solution of phenylalanine methyl ester, admixing it 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-benzyloxycarbonyl aspartic acid with phenylalanine methyl ester to deposit an addition compound of N-benzyloxycarbonyl-α-L-aspartyl-L-phenylalanine methyl ester and phenylalanine methyl ester and recovering the addition compound.

Workup

  1. customto prepare a solution

Sources & evidence

ORD record
ord-443e4dd4021f4f8b86e10ac05395b542
Source dataset
uspto-grants-1985_06
Patent number
US04521514

Reaction notes

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