化工社化工社 化学情報印刷レポート · 研究参考用
tert-Butanol → 4-Benzyloxycarbonylamino-cyclohexanecarboxylic acid tert-butyl ester
関与物質
| 役割 | 名称 | HCID | 仕込み量 |
|---|---|---|---|
| 反応物 | tert-Butanol | HCID 6386 | — |
| 反応物 | Diisopropylcarbodiimide | HCID 12734 | — |
| 反応物 | 4-(((Benzyloxy)(hydroxy)methylidene)amino)cyclohexane-1-carboxylic acid | HCID 285247 | — |
| 触媒 | 4-(Dimethylamino)pyridine | HCID 14284 | — |
| 溶媒 | Dimethylformamide | HCID 6228 | — |
| 溶媒 | Dichloromethane | HCID 6344 | — |
| 生成物 | 4-Benzyloxycarbonylamino-cyclohexanecarboxylic acid tert-butyl ester | HCID 53888193 | 54.2% |
反応手順
To a solution of 4-benzyloxycarbonylamino-cyclohexanecarboxylic acid (8.0 g, 28.78 mmol) in DCM (35 mL) and DMF (35 mL) is added t-butanol (10 mL, 105.4 mmol) and DMAP (1.4 g, 11.50 mmol). DIPC (10 mL) is added portionwise over 1 h. The resulting mixtures stirs 18 h. The mixture is mounted onto SiO2 and purified by flash chromatography (gradient elution: 0-60% EtOAc/Hep) which affords 5.2 g of 4-benzyloxycarbonylamino-cyclohexanecarboxylic acid tert-butyl ester. 1H NMR (400 MHz, DMSO-D6) δ ppm 1.14 (m, 2 H) 1.30 (m, 2 H) 1.38 (m, 9 H) 1.82 (m, 4 H) 2.07 (m, 1 H) 3.20 (m, 1 H) 3.47 (m, 3 H) 4.99 (m, 2 H) 7.27 (m, 5 H).
情報源と証拠
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| 特許番号 | US08476224B2 |
| 出典データセット | uspto-grants-2013_07 |
| ORD ID | ord-64d3637cf11f405ebc08fa57c9171a4e |
| 出典メモ | uspto-grants-2013_07 |