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4-Methylmorpholine → N-(t-butyloxy)-2(R)-[[4-methoxybenzenesulfonyl]-amino]-3(R)-hydroxybutanamide
関与物質
| 役割 | 名称 | HCID | 仕込み量 |
|---|---|---|---|
| 反応物 | 4-Methylmorpholine | HCID 7972 | — |
| 反応物 | 1-Hydroxybenzotriazole | HCID 75771 | — |
| 反応物 | N-[4-methoxybenzenesulfonyl]-(D)-threonine | HCID 2104039 | — |
| 反応物 | 1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride | HCID 2723939 | — |
| 反応物 | O-tert-butylhydroxylamine hydrochloride | HCID 2777906 | — |
| 溶媒 | Water | HCID 962 | — |
| 溶媒 | Dichloromethane | HCID 6344 | — |
| 生成物 | N-(t-butyloxy)-2(R)-[[4-methoxybenzenesulfonyl]-amino]-3(R)-hydroxybutanamide | HCID 22856309 | — |
反応手順
N-[4-methoxybenzenesulfonyl]-(D)-threonine (4.0 g, 13.84 mmol), 1-hydroxybenzotriazole (1.87 g, 13.84 mmol), 4-methylmorpholine (7.9 mL, 69.2 mmol), and O-t-butylhydroxylamine hydrochloride (5.22 g, 41.52 mmol) are dissolved in methylene chloride (100 mL). To this solution is added N-[dimethylaminopropyl]-N'-ethylcarbodiimide hydrochloride (3.45 g, 17.99 mmol), and the reaction is stirred overnight. The mixture is then diluted with water and extracted with methylene chloride. The combined organic extracts are washed with brine, dried (Na2SO4), and concentrated in vacuo. The crude product is purified by silica gel chromatography (ethyl acetate) to give N-(t-butyloxy)-2(R)-[[4-methoxybenzenesulfonyl]amino]-3(R)-hydroxybutanamide.
情報源と証拠
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| 特許番号 | US05455258 |
| 出典データセット | uspto-grants-1995_10 |
| ORD ID | ord-ba402cf3c8584f16a46d82c4784f7ae4 |
| 出典メモ | uspto-grants-1995_10 |