Acetonitrile → N-benzoyl-L-aspartyl-L-phenylalanine methyl ester

HRID 36838

Reaction equation

HRID 36838 reaction equation
[C:1]([NH:9][C@H:10]([C:15]([OH:17])=O)[CH2:11][C:12]([OH:14])=[O:13])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:18][O:19][C:20](=[O:30])[C@H:21]([CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[NH2:22].C(#N)C.[OH-].[Na+]>O>[CH3:18][O:19][C:20](=[O:30])[C@H:21]([CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[NH:22][C:15](=[O:17])[C@H:10]([CH2:11][C:12](=[O:13])[OH:14])[NH:9][C:1](=[O:8])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 6342AcetonitrileHCID 14798Sodium HydroxideHCID 205448N-Benzoyl-L-aspartic acidHCID 736234L-Phenylalanine, methyl ester

Product 1

HCID 22853567N-benzoyl-L-aspartyl-L-phenylalanine methyl ester

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
40 °C

Procedure

1.19 g (5.0 mmol) of N-benzoyl-L-aspartic acid and 1.79 g (10.0 mmol) of L-phenylalanine methyl ester were added to a flask which contained 50 ml of 50% acetonitrile in water containing 5 mM CaCl2. The pH of the solution was adjusted to 6.0 with 10M NaOH. The solution was admixed with 4 g of suction filtered immobilized enzyme prepared above. Thereafter, the reaction were carried out with stirring for 4 hours at 40° C. After completion of the reaction, the immobilized enzyme was separated by filtration. The pH of the filtrate was then adjusted to 3.7 by 10 molar hydrochloric acid. Resulting slurry was filtered and washed with water to give N-benzoyl-L-aspartyl-L-phenylalanine methyl ester.

Workup

  1. filtrationfiltered immobilized enzyme
  2. customprepared above
  3. customAfter completion of the reaction
  4. customthe immobilized enzyme was separated by filtration
  5. customResulting slurry
  6. filtrationwas filtered
  7. washwashed with water

Sources & evidence

ORD record
ord-2eef8a023524429e8e2b053fe98d2fb8
Source dataset
uspto-grants-1995_05
Patent number
US05418146

Linked notes

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