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Triethylamine → trans-2-(Methylpropylcarbamoyl)-cyclopropane carboxylic acid ethyl ester
関与物質
| 役割 | 名称 | HCID | 仕込み量 |
|---|---|---|---|
| 反応物 | Triethylamine | HCID 8471 | — |
| 反応物 | N-Methylpropylamine | HCID 12315 | — |
| 反応物 | 1-Hydroxybenzotriazole | HCID 75771 | — |
| 反応物 | 1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride | HCID 2723939 | — |
| 反応物 | (1R,2R)-2-(ethoxycarbonyl)cyclopropane-1-carboxylic acid | HCID 11535603 | — |
| 溶媒 | Dimethylformamide | HCID 6228 | — |
| 生成物 | trans-2-(Methylpropylcarbamoyl)-cyclopropane carboxylic acid ethyl ester | HCID 68561965 | 50% |
反応手順
Add 1-hydroxybenzotriazole (HOBT) (1.46 g, 10.8118 mmol), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (EDCI) (2.07 g, 10.8118 mmol) to a solution of crude trans-cyclopropane-1,2-dicarboxylic acid monoethyl ester (1.71 g, 10.8118 mmol) in N,N-dimethylformamide (11 mL). Stir for 30 minutes. Add triethylamine (2.26 mL, 16.2177 mmol) and methylpropylamine (1.11 mL, 10.8118 mmol) and stir for 16 hours. Quench with 10% aqueous potassium carbonate (10 mL) and extract with ethyl acetate (3×50 mL). Combine the organic extracts, wash with 0.1 N aqueous citric acid (30 mL) and 1 N lithium chloride, dry (magnesium sulfate), concentrate and crystallize with xylenes to give the desired compound (1.02 g, 50%).
情報源と証拠
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| 特許番号 | US07745438B2 |
| 出典データセット | uspto-grants-2010_06 |
| ORD ID | ord-d627f1bf619d45f9a308e90a73367594 |
| 出典メモ | uspto-grants-2010_06 |