HuagongsheHuagongshe Chemistry Print Report · For research reference only
Cesium carbonate → N-Methyl-2-{2-[(2S)-oxiran-2-ylmethoxy]phenyl}acetamide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Cesium carbonate | HCID 10796 | — |
| Reactant | Benzenesulfonic acid, 3-nitro-, (2S)-2-oxiranylmethyl ester | HCID 146490 | — |
| Reactant | 2-(2-hydroxyphenyl)-N-methylacetamide | HCID 21712311 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | N-methyl-2-pyrrolidone | HCID 13387 | — |
| Product | N-Methyl-2-{2-[(2S)-oxiran-2-ylmethoxy]phenyl}acetamide | HCID 86612852 | 28.9% |
Reaction Steps
A mixture of 2-(2-hydroxyphenyl)-N-methylacetamide (1.00 g, 6.1 mmol) prepared according to a known procedure (Bernd, Peschke, Eur. J. Med. Chem., 2000, 35, 599-618), (2S)-oxiran-2-ylmethyl 3-nitrobenzenesulfonate (1.58 g, 6.1 mmol) and cesium carbonate (2.37 g, 7.3 mmol) in 1-methylpyrrolidin-2-one (15 ml) was stirred at room temperature overnight. The mixture was diluted with water and extracted with ethyl acetate, the combined organic layers were dried with sodium sulphate, volatiles were removed in vacuo. The residue was purified by recrystillaziation from ethyl acetate/heptane; (390 mg) of the subtitle compound was obtained.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07498338B2 |
| Source dataset | uspto-grants-2009_03 |
| ORD ID | ord-114f061e04114a049b83470f3a2890ef |
| Source note | uspto-grants-2009_03 |