HuagongsheHuagongshe Chemistry Print Report · For research reference only
Methyl propiolate → (S)-N-[[3-[3-Fluoro-4-(4-carbomethoxy-1H-1,2,3-triazol-1-yl)phenyl]-2-oxo-5-oxazolidinyl]methyl]acetamide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Methyl propiolate | HCID 13536 | — |
| Reactant | (S)-N-[[3-[4-Azido-3-fluorophenyl]-2-oxo-5-oxazolidinyl]methyl]acetamide | HCID 10708829 | — |
| Solvent | Benzene | HCID 241 | — |
| Product | (S)-N-[[3-[3-Fluoro-4-(4-carbomethoxy-1H-1,2,3-triazol-1-yl)phenyl]-2-oxo-5-oxazolidinyl]methyl]acetamide | HCID 10714593 | 68.6% |
Reaction Steps
A solution 1.0 g (3.4 mmol) of the azide of Example 17 in 50 mL benzene was treated with 573 mg (6.8 mmol) of methyl propiolate followed by warming at reflux for 24 h. The mixture was cooled and the product isolated by filtration of the reaction mixture. These procedures afforded 880 mg of the title compound as a white solid. High Resolution Mass Spectrum (EI): calcd for C16H16FN5O5 : 377.1135. found: 377.1131.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US05910504 |
| Source dataset | uspto-grants-1999_06 |
| ORD ID | ord-64aaff22c4ae4f9690f58c722482a856 |
| Source note | uspto-grants-1999_06 |