HuagongsheHuagongshe Chemistry Print Report · For research reference only
Hydrochloric Acid → 4,4-dimethyl-4H,6H,7H-pyrano[4,3-d][1,3]thiazol-2-amine
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Hydrochloric Acid | HCID 313 | — |
| Reactant | Sodium Hydroxide | HCID 14798 | — |
| Reactant | Tert-butyl 5-(1-hydroxy-1-methylethyl)-4-[2-(tetrahydro-2h-pyran-4-yloxy)ethyl]-1,3-thiazol-2-ylcarbamate | HCID 87745649 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | 4,4-dimethyl-4H,6H,7H-pyrano[4,3-d][1,3]thiazol-2-amine | HCID 87179372 | 51.3% |
Reaction Steps
To a solution of Example 3D (4.6 g, 11 mmol) in tetrahydrofuran was added conc. HCl (6.9 mL). The reaction mixture was refluxed overnight and then cooled to room temperature. The mixture was basified with 5N NaOH (17 mL) and extracted with ethyl acetate (3×50 mL). The combined organic extracts were dried (Na2SO4), filtered and concentrated. The residue was purified by column chromatography using an Analogix® IT280™ (SiO2, 0-10% methanol in dichloromethane to afford 1.04 g (51%) of the title compound. MS (ESI+) m/z 185 (M+H)+
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08735434B2 |
| Source dataset | uspto-grants-2014_05 |
| ORD ID | ord-4d271d94be87446092c4fc238530debb |
| Source note | uspto-grants-2014_05 |