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Hydrochloric Acid → (S)-3-(5-chloroindole-2-carbonylamino)-1-cyanomethyl-3,4-dihydrocarbostyril
関与物質
| 役割 | 名称 | HCID | 仕込み量 |
|---|---|---|---|
| 反応物 | Hydrochloric Acid | HCID 313 | — |
| 反応物 | Bromoacetonitrile | HCID 11534 | — |
| 反応物 | Sodium Methoxide | HCID 10942334 | — |
| 反応物 | (S)-3-(5-chloroindole-2-carbonylamino)-3,4-dihydrocarbostyril | HCID 44357926 | — |
| 溶媒 | Water | HCID 962 | — |
| 溶媒 | Tetrahydrofuran | HCID 8028 | — |
| 溶媒 | Ethyl Acetate | HCID 8857 | — |
| 生成物 | (S)-3-(5-chloroindole-2-carbonylamino)-1-cyanomethyl-3,4-dihydrocarbostyril | HCID 87730389 | 26.8% |
反応手順
(S)-3-(5-chloroindole-2-carbonylamino)-3,4-dihydrocarbostyril (Example 4, 13.4 mg) was dissolved in tetrahydrofuran (5 mL) at room temperature under argon with stirring. After cooing to 0° C., sodium methoxide (4.3 mg) was added, followed 2 h later by bromoacetonitrile (7.2 mg). This was warmed to room temperature over 2 h, and 2 h later water (15 mL), 1.0 M aqueous hydrochloric acid (1 mL), and ethyl acetate (20 mL) were added. The organic phase was separated, washed with brine, and dried over anhydrous sodium sulfate. After solvent evaporation under vacuum, the crude product was purified by reverse phase preparative HPLC to provide the title compound (4 mg). HPLC/MS [M+H]+, 379; HPLC/MS [M+Na]+, 401.
情報源と証拠
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| 特許番号 | US07425550B2 |
| 出典データセット | uspto-grants-2008_09 |
| ORD ID | ord-5f52219d11a3463cbd7e28dea8f852c5 |
| 出典メモ | uspto-grants-2008_09 |