Ammonia → (αS)-α-Methyl-4-(2-methylpropyl)benzeneacetamide

HRID 1612940Notes

Reaction equation

HRID 1612940 reaction equation
[OH:1][C:2]([C@H:4]([C:6]1[CH:15]=[CH:14][C:9]([CH2:10][CH:11]([CH3:13])[CH3:12])=[CH:8][CH:7]=1)[CH3:5])=O.C(C1C=CC([C@H](C)C(Cl)=O)=CC=1)C(C)C.C(Cl)(=O)C(Cl)=O.[Cl-].[NH3:38]>>[CH2:10]([C:9]1[CH:14]=[CH:15][C:6]([C@H:4]([CH3:5])[C:2]([NH2:38])=[O:1])=[CH:7][CH:8]=1)[CH:11]([CH3:13])[CH3:12]

Participants

6

Reactant 5

HCID 222AmmoniaHCID 312ChlorideHCID 39912DexibuprofenHCID 65578Oxalyl chlorideHCID 10609225(αS)-α-Methyl-4-(2-methylpropyl)benzeneacetyl chloride

Product 1

HCID 715796(αS)-α-Methyl-4-(2-methylpropyl)benzeneacetamide

Procedure

The above hydrolysis procedure gives about 2% racemization demonstrated by: (1) converting a sample of (S)-(+)-ibuprofen (98.6% S enantiomer by HPLC) to (S)-(+)-2-(4-isobutylphenyl)propanoyl chloride with oxalyl chloride; (2) treating the chloride with ammonia to obtain (S)-(+)-2-(4-isobutylphenyl)propionamide; and (3) hydrolyzing the amide as described above to regenerate (S)-(+)-ibuprofen (96.6% S enantiomer by HPLC).

Workup

  1. customThe above hydrolysis procedure
  2. customgives about 2% racemization

Sources & evidence

ORD record
ord-93e4f5e8f5664d09b8c0cdd3d91d1297
Source dataset
uspto-grants-1993_03
Patent number
US05191095

Reaction notes

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