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2,4,6-Trimethylpyridine → (4R)-N-[(1S)-1-Methyl-2-nitroxyethyl]-2-oxothiazolidin-4-yl-carboxamide
関与物質
| 役割 | 名称 | HCID | 仕込み量 |
|---|---|---|---|
| 反応物 | 2,4,6-Trimethylpyridine | HCID 7953 | — |
| 反応物 | Nitronium tetrafluoroborate | HCID 11073463 | — |
| 反応物 | (4R)-N-[(1S)-1-Methyl-2-hydroxyethyl]-2-oxothiazolidin-4-yl-carboxamide | HCID 21309140 | — |
| 溶媒 | Acetonitrile | HCID 6342 | — |
| 生成物 | (4R)-N-[(1S)-1-Methyl-2-nitroxyethyl]-2-oxothiazolidin-4-yl-carboxamide | HCID 9816362 | 29.2% |
反応手順
In 10 ml of dry acetonitrile were dissolved 478 mg of nitronium tetrafluoroboron (85% content), 0.43 ml of 2,4,6-collidine was added thereto with stirring under ice-cooling, and the mixture was stirred under ice-cooling for 30 minutes. To the resulting mixture were added 500 mg of (4R)-N-[(1S)-1-methyl-2-hydroxyethyl]-2-oxothiazolidin-4-yl-carboxamide, and the mixture was stirred at room temperature for 1 hour and 45 minutes. Then, the solvent was distilled off under reduced pressure and the thus obtained residue was purified by silica gel column chromatography employing cyclohexane-ethyl acetate (3:7) as an eluent to obtain 178 mg of the desired compound as colorless crystals.
情報源と証拠
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| 特許番号 | US05891898 |
| 出典データセット | uspto-grants-1999_04 |
| ORD ID | ord-e09145e95582489a842ab3d05043dfe5 |
| 出典メモ | uspto-grants-1999_04 |