関与物質
| 役割 | 名称 | HCID | 仕込み量 |
|---|
| 反応物 | Hydrochloric Acid | HCID 313 | — |
| 反応物 | tert-Butanol | HCID 6386 | — |
| 反応物 | 1,1'-Carbonyldiimidazole | HCID 68263 | — |
| 反応物 | 1,8-Diazabicyclo(5.4.0)undec-7-ene | HCID 81184 | — |
| 反応物 | 4-Thiazolecarboxylic acid | HCID 304271 | — |
| 溶媒 | Water | HCID 962 | — |
| 溶媒 | Dimethylformamide | HCID 6228 | — |
| 生成物 | Tert-butyl 1,3-thiazole-4-carboxylate | HCID 16744294 | 47% |
反応手順
To a solution of thiazole-4-carboxylic acid 7.1 (1 g, 7.2 mmol) and carbonyldiimidazole (6.3 g, 38.7 mmol) in commercial dry DMF (50 mL) under N2 was stirred at 50° C. for 20 min. Tert-butanol (8.6 g, 116.0 mmol) and DBU (5.8 mL, 38.7 mmol) were then successively added at once and the reaction was warmed at 60° C. for 48 h. The RM was then allowed to cool down to RT and the pH was adjusted to 4 with a solution of HCl (2M, ˜80 mL). The mixture was diluted with water (250 mL) and extracted with Et2O (3×100 mL). The combined org. layers were washed with brine (250 mL), dried over MgSO4, concentrated and purified on silica gel using DCM to afford title product as yellowish oil (47%). Yield: 3.37 g (47%). LCMS: P=98%, rt=3.65 nm, m/z=186.
情報源と証拠
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| 特許番号 | US08871761B2 |
|---|
| 出典データセット | uspto-grants-2014_10 |
|---|
| ORD ID | ord-beb5a80539924462b21bb4ef310f3bf3 |
|---|
| 出典メモ | uspto-grants-2014_10 |
|---|
