HuagongsheHuagongshe Chemistry Print Report · For research reference only
Ammonium Acetate → (S)-N-{3-[4-(4-(1-Cyano-cyclopropylmethylidene)-piperidin-1-yl)-3-fluorophenyl]-2-oxo-oxazolidin-5-ylmethyl}-acetamide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Ammonium Acetate | HCID 517165 | — |
| Reactant | Cyclopropylacetonitrile | HCID 643447 | — |
| Reactant | N-[(5S)-3-[3-fluoro-4-(4-oxopiperidinyl)phenyl]-2-oxo-5-oxazolidinyl]methylacetamide | HCID 54375226 | — |
| Solvent | Toluene | HCID 1140 | — |
| Product | (S)-N-{3-[4-(4-(1-Cyano-cyclopropylmethylidene)-piperidin-1-yl)-3-fluorophenyl]-2-oxo-oxazolidin-5-ylmethyl}-acetamide | HCID 69312101 | 69% |
Reaction Steps
The mixture of (S)-N-{3-[4-(4-oxo-piperidin-1-yl)-3-fluorophenyl]-2-oxo-oxazolidin-5-ylmethyl}-acetamide (2.86 mmol), cyclopropylacetonitrile (5.73 mmol), ammonium acetate (catalytic) in 100 ml of toluene was heated at reflux temperature for 5 to 6 hours. The reaction mixture was cooled to room temperature and extracted with ethyl acetate water mixture, dried and evaporated to give crude product. The crude product was recrystallized from ethyl acetate to furnish title compound in 69% yield.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07405228B2 |
| Source dataset | uspto-grants-2008_07 |
| ORD ID | ord-9afbb5837de94abc90f0dfb3b34b7efb |
| Source note | uspto-grants-2008_07 |