HuagongsheHuagongshe Chemistry Print Report · For research reference only
Cesium carbonate → (4S)-3-((3S)-3-(3-Isoxazolyl)-3-(4-(((3-methyl-5-(4-(trifluoromethyl)phenyl)-2-thienyl)methyl)oxy)phenyl)propanoyl)-4-(phenylmethyl)-1,3-oxazolidin-2-one
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Cesium carbonate | HCID 10796 | — |
| Reactant | 2-(Chloromethyl)-3-methyl-5-[4-(trifluoromethyl)phenyl]thiophene | HCID 15946281 | — |
| Reactant | (S)-4-Benzyl-3-((S)-3-(4-hydroxyphenyl)-3-(isoxazol-3-yl)propanoyl)oxazolidin-2-one | HCID 57801829 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | (4S)-3-((3S)-3-(3-Isoxazolyl)-3-(4-(((3-methyl-5-(4-(trifluoromethyl)phenyl)-2-thienyl)methyl)oxy)phenyl)propanoyl)-4-(phenylmethyl)-1,3-oxazolidin-2-one | HCID 59300606 | 76.5% |
Reaction Steps
A mixture of 62.7 (0.23 mmol), 7.5 (76 mg, 0.19 mmol), and Cs2CO3 (226 mg, 0.69 mmol) in DMF (2.3 mL) was stirred overnight at room temperature. The mixture was diluted with EtOAc, washed with water and brine, dried (Na2SO4), and concentrated. The crude product was chromatographed on silica gel (15-45% EtOAc/hexane) to afford 62.8 (94 mg, 75%) as a white solid.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08003648B2 |
| Source dataset | uspto-grants-2011_08 |
| ORD ID | ord-ad1aaa2bf09b486ebd4bff2e7a8a7b72 |
| Source note | uspto-grants-2011_08 |