Ammonia → Dexibuprofen

HRID 1974442

Reaction equation

HRID 1974442 reaction equation
P([O-])([O-])([O-])=O.[K+].[K+].[K+].C(C1C=CC(C(C)C#N)=CC=1)C(C)C.[CH2:23]([C:27]1[CH:32]=[CH:31][C:30]([CH:33]([CH3:37])[C:34]([OH:36])=[O:35])=[CH:29][CH:28]=1)[CH:24]([CH3:26])[CH3:25].N>>[CH3:37][C@H:33]([C:34]([OH:36])=[O:35])[C:30]1[CH:31]=[CH:32][C:27]([CH2:23][CH:24]([CH3:25])[CH3:26])=[CH:28][CH:29]=1

Participants

5

Reactant 4

HCID 222AmmoniaHCID 3672Ibuprofen, (+-)-HCID 62657Potassium Phosphate, TribasicHCID 1083742-(4-Isobutylphenyl)propiononitrile2×

Product 1

HCID 39912Dexibuprofen

Conditions

Temperature
32 °C

Procedure

One ml of the reaction solution containing 100 μmol of potassium phosphate buffer solution (pH 8.0), 4.77 μmol of 2-(4'-isobutylphenyl)propionitrile and 0.02 unit of nitrilase was thoroughly shaken at 32° C. to carry out the reaction. The amounts of 2-(4'-isobutylphenyl)-propionitrile, 2-(4'-isobutylphenyl)propionic acid and ammonia for each reaction time were determined. The results are shown in the Figure. The optical purity of the formed S-(+)-2-(4'-isobutylphenyl)propionic acid was 98% for 6 hours, 96% for 24 hours and 95% for 40 hours.

Workup

  1. customthe reaction
  2. customfor 6 hours
  3. wait95% for 40 hours

Sources & evidence

ORD record
ord-a910e50445e34748afab0963e9b6fb00
Source dataset
uspto-grants-1994_02
Patent number
US05283193

Linked notes

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