HuagongsheHuagongshe Chemistry Print Report · For research reference only
2,6-Di-tert-butylpyridine → 5-(S)-Acetamidomethyl-3-[4'-formamido-3'-fluorophenyl]oxazolidine-2-one
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 2,6-Di-tert-butylpyridine | HCID 68510 | — |
| Reactant | 4-Nitrophenyl formate | HCID 74628 | — |
| Reactant | (S)-N-[3-[3-Fluoro-4-aminophenyl]-2-oxo-5-oxazolidinyl]methylacetamide | HCID 10778218 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | 5-(S)-Acetamidomethyl-3-[4'-formamido-3'-fluorophenyl]oxazolidine-2-one | HCID 22966190 | 85.1% |
Reaction Steps
A solution of 5-(S)-acetamidomethyl-3-[4′-amino-3′-fluorophenyl]-oxazolidine-2-one (0.200 g, 0.748 mmol), p-nitrophenyl formate (0.188 g, 1.12 mmol), and 2,6-di-(tert-butyl)pyridine (0.336 mL, 1.50 mmol) in THF (4 mL) was stirred at 65° C. overnight. Solvent was removed under vacuum and the residue purified by PTLC (30% acetone in DCM) to give product as a white solid (0.188 g, 85%). M.p. 196-8° C.; MS (m/z): [M+H]+=296.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US06743811B2 |
| Source dataset | uspto-grants-2004_06 |
| ORD ID | ord-77e4da8371a04de5a609669748cff5be |
| Source note | uspto-grants-2004_06 |