HuagongsheHuagongshe Chemistry Print Report · For research reference only
Water → Ethyl 2-(2-thioxo-2,3-dihydrobenzoxazol-5-yl)propionate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Phenyl thioxochloroformate | HCID 70498 | — |
| Reactant | 1,8-Diazabicyclo(5.4.0)undec-7-ene | HCID 81184 | — |
| Reactant | Ethyl 3-amino-4-hydroxy-phenyl-propionate | HCID 12202638 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | Ethyl 2-(2-thioxo-2,3-dihydrobenzoxazol-5-yl)propionate | HCID 20319623 | — |
Reaction Steps
A solution of 2-(3-amino-4-hydroxy-phenyl)-propionic acid ethyl ester (370 mg) in DMF (2 mL) was added phenyl chlorothionoformate (380 mg in DMF), and DBU (540 mg, in DMF) at room temperature. The reaction mixture was stirred for 16 h at room temperature and water was added to this mixture. The resulting mixture was extracted with ethyl ether. The combined organic layer was dried over magnesium sulfate, filtered and concentrated in vacuo. The resulting residue was chromatographed on silica gel (n-Hex:EtOAc=4:1) to afford the product as white solid. (130 mg, 29.2%)
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08084484B2 |
| Source dataset | uspto-grants-2011_12 |
| ORD ID | ord-d47d54ef4c0341d2af21bb3d8816303e |
| Source note | uspto-grants-2011_12 |