Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Sodium hydride | HCID 24758 | — |
| Reactant | Phenyl cyanate | HCID 70740 | — |
| Reactant | HCID 66975082 | HCID 66975082 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 86663881 | HCID 86663881 | 53.5% |
Reaction Steps
To a solution of tert-butyl (6R,7R)-7-(4-chloro-3-fluorophenyl)-6-[(2-oxotetrahydropyrimidin-1(2H)-yl)methyl]-1,4-oxazepane-4-carboxylate (260 mg) in DMF (2.9 mL) was added sodium hydride (94.0 mg, 60% in oil) under ice-cooling, and the mixture was stirred at 0° C. for 1 hr, and at room temperature for 1 hr. Then, phenyl cyanate (210 mg) was added, and the mixture was stirred at room temperature for 1 hr. To the reaction mixture was added distilled water, and the mixture was extracted with ethyl acetate. The obtained extract was washed with distilled water and brine, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel chromatography (hexane/ethyl acetate) to give the title compound (147 mg).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US08722662B2 |
|---|
| Source dataset | uspto-grants-2014_05 |
|---|
| ORD ID | ord-9611ce1a71e149e3940fa87901013ea4 |
|---|
| Source note | uspto-grants-2014_05 |
|---|