Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Ethanol | HCID 702 | — |
| Reactant | Ethyl bromopyruvate | HCID 66144 | — |
| Reactant | HCID 87398339 | HCID 87398339 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 45380498 | HCID 45380498 | — |
Reaction Steps
To a stirred solution of (2R,4S,4aS)-rel-11-fluoro-2,4-dimethyl-2′,4′,6′-trioxo-1,1′,2,3′,4,4′,4a,6′-octahydro-2′H,6H-spiro[1,4-oxazino[4,3-a][1,2]oxazolo[4,5-g]quinoline-5,5′-pyrimidine]-8-carbothioamide (Intermediate 575, 54 mg, 0.128 mmol) in mixture of EtOH:DMF (1 mL: 0.5 mL) were added ethyl bromopyruvate (47 mg, 0.24 mmol) and molecular sieves, and the mixture was stirred at 100° C. for 12 hours. The reaction mixture was concentrated, the residue was purified by silica gel column chromatography to give product as solid. Yield: 13 mg (20%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US09040528B2 |
|---|
| Source dataset | uspto-grants-2015_05 |
|---|
| ORD ID | ord-4675ead5cf984fc6a217033b68fbe7b7 |
|---|
| Source note | uspto-grants-2015_05 |
|---|