HuagongsheHuagongshe Chemistry Print Report · For research reference only
Ammonia → (αS)-α-Methyl-4-(2-methylpropyl)benzeneacetamide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Ammonia | HCID 222 | — |
| Reactant | Chloride | HCID 312 | — |
| Reactant | Dexibuprofen | HCID 39912 | — |
| Reactant | Oxalyl chloride | HCID 65578 | — |
| Reactant | (αS)-α-Methyl-4-(2-methylpropyl)benzeneacetyl chloride | HCID 10609225 | — |
| Product | (αS)-α-Methyl-4-(2-methylpropyl)benzeneacetamide | HCID 715796 | — |
Reaction Steps
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).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US05191095 |
| Source dataset | uspto-grants-1993_03 |
| ORD ID | ord-93e4f5e8f5664d09b8c0cdd3d91d1297 |
| Source note | uspto-grants-1993_03 |