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Triethylamine → (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 | Triethylamine | HCID 8471 | — |
| 反応物 | Procysteine | HCID 72390 | — |
| 反応物 | P,P-Diphenylphosphinic azide | HCID 199401 | — |
| 反応物 | (1S)-1-Methyl-2-nitroxyethylamine hydrochloride | HCID 86754033 | — |
| 溶媒 | Tetrahydrofuran | HCID 8028 | — |
| 生成物 | (4R)-N-[(1S)-1-Methyl-2-nitroxyethyl]-2-oxothiazolidin-4-yl-carboxamide | HCID 9816362 | 94.2% |
反応手順
In 60 ml of dry tetrahydrofuran were suspended 2.06 g of (4R)-2-oxothiazolidine-4-carboxylic acid and 2.00 g of (1S)-1-methyl-2-nitroxyethylamine hydrochloride, 4.5 ml of triethylamine and 3.00 ml of diphenylphosphoryl azide were added thereto with stirring under ice-cooling, and the mixture was stirred at room temperature for 5 hours. Then, the solvent was distilled off under reduced pressure and the residue was purified by silica gel column chromatography employing cyclohexane-ethyl acetate (1:4) as an eluent to obtain 3.00 g of colorless crystals. The crystals were recrystallized from ethyl acetate to obtain 0.964 g of the desired compound as colorless needle crystals.
情報源と証拠
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| 特許番号 | US05925658 |
| 出典データセット | uspto-grants-1999_07 |
| ORD ID | ord-92c3c08958e34ac08653b24b825b3693 |
| 出典メモ | uspto-grants-1999_07 |