L-Aspartic Acid → L-Phenylalanine, methyl ester

HRID 1248001Notes

Reaction equation

HRID 1248001 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

Accordingly, this invention provide a process for producing an addition compound of a dipeptide ester and an amino acid ester, in which aspartic acid and benzyloxycarbonyl chloride is reacted in an aqueous solution in the presence of a base to prepare a solution containing N-benzyloxycarbonyl aspartic acid; phenylalanine and methanol are separatedly reacted in the presence of an acid to produce phenylalanine methyl ester; excess methanol is substituted with water to convert it to an aqueous solution of phenylalanine methyl ester; it is admixed with the above-prepared aqueous solution containing N-benzyloxycarbonyl aspartic acid; an proteolytic enzyme is added into the resulting mixture under conditions, under which no substantial deactivation of the enzyme occurrs; N-benzyloxycarbonyl aspartic acid and phenylalanine methyl ester are reacted under conditions, under which the proteolytic enzyme exerts the enzymatic activity, to deposit an addition compound of N-benzyloxycarbonyl-α-L-aspartyl-L-phenylalanine methyl ester and phenylalanine methyl ester; and then the addition compound is recovered.

Workup

  1. customto prepare a solution

Sources & evidence

ORD record
ord-40935e9937d643e39337b150596d7846
Source dataset
uspto-grants-1985_06
Patent number
US04521514

Reaction notes

Loading…