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Pyridine → (R,R)-N-[3-(4-hydroxyphenyl)-4-methylisothiazol-5-yl]-2-methylcyclopropanecarboxamide
関与物質
| 役割 | 名称 | HCID | 仕込み量 |
|---|---|---|---|
| 反応物 | Pyridine | HCID 1049 | — |
| 反応物 | Dichloromethane | HCID 6344 | — |
| 反応物 | Oxalyl chloride | HCID 65578 | — |
| 反応物 | rel-(1R,2R)-2-Methylcyclopropanecarboxylic acid | HCID 6995705 | — |
| 反応物 | 4-(5-Amino-4-methylisothiazol-3-yl)phenol | HCID 136355285 | — |
| 触媒 | Dimethylformamide | HCID 6228 | — |
| 溶媒 | Toluene | HCID 1140 | — |
| 溶媒 | Tetrahydrofuran | HCID 8028 | — |
| 溶媒 | Ethyl Acetate | HCID 8857 | — |
| 生成物 | (R,R)-N-[3-(4-hydroxyphenyl)-4-methylisothiazol-5-yl]-2-methylcyclopropanecarboxamide | HCID 136244237 | 64.6% |
反応手順
Add oxalyl chloride (2 M in dichloromethane, (0.291 mL, 0.583 mmol) to a stirred solution of (R,R)-2-methylcyclopropanecarboxylic acid (0.06 g, 0.58 mmol) and DMF (1 drop-catalytic) in toluene (1 mL). Stir 3 h and add the now formed acid chloride to a stirred solution of 4-(5-amino-4-methylisothiazol-3-yl)phenol (0.060 g, 0.291 mmol) and pyridine (0.07 g, 0.87 mmol) in THF (1 mL). Stir 1 h and dilute with EtOAc (300 mL), and wash with 1 N NaOH (2 times 100 mL) then water (100 mL), dry (MgSO4) and evaporate. Crystallize from chloroform and hexane. Yield: 64.6%. ES-MS: m/e 289.0 (m+1).
情報源と証拠
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| 特許番号 | US07960419B2 |
| 出典データセット | uspto-grants-2011_06 |
| ORD ID | ord-ad34b95702754957aa30c7779bafce6d |
| 出典メモ | uspto-grants-2011_06 |