HuagongsheHuagongshe Chemistry Print Report · For research reference only
Hydrochloric Acid → {7-Bromo-4-[3-oxo-3,4-dihydro-2H-1,4-benzoxazin-6-carbonyl]-3,4-dihydro-2H-1,4-benzoxazin-3-yl}acetic acid
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Hydrochloric Acid | HCID 313 | — |
| Reactant | Lithium Hydroxide | HCID 3939 | — |
| Reactant | Ethyl Acetate | HCID 8857 | — |
| Reactant | Ethyl {7-bromo-4-[(3-oxo-3,4-dihydro-2H-1,4-benzoxazin-6-yl)carbonyl]-3,4-dihydro-2H-1,4-benzoxazin-3-yl}acetate | HCID 131736333 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | {7-Bromo-4-[3-oxo-3,4-dihydro-2H-1,4-benzoxazin-6-carbonyl]-3,4-dihydro-2H-1,4-benzoxazin-3-yl}acetic acid | HCID 118599755 | 108% |
Reaction Steps
LiOH (55.3 mg, 2.31 mmol) dissolved in water (3 mL) was added to a solution of ethyl {7-bromo-4-[(3-oxo-3,4-dihydro-2H-1,4-benzoxazin-6-yl)carbonyl]-3,4-dihydro-2H-1,4-benzoxazin-3-yl}acetate (Intermediate 28, 366 mg, 0.77 mmol) in THF (6.0 mL). The mixture was stirred at rt for 1.5 h. EtOAc (40 mL) was added followed by 1 M HCl (3.1 mL, 3.1 mmol) and water (20 mL). The phases were separated and the organic layer was washed with brine (30 mL), dried over Na2SO4 and evaporated to give crude title compound (372 mg, 108%) as a solid.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09394291B2 |
| Source dataset | uspto-grants-2016_07 |
| ORD ID | ord-cd9d5e4df2d14a729317bf13df1c674f |
| Source note | uspto-grants-2016_07 |