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Water → 4-[2-(tert-butoxycarbonylamino)ethoxy]-3-methoxy-N-(3-phenylphenyl)phenylacetamide
関与物質
| 役割 | 名称 | HCID | 仕込み量 |
|---|---|---|---|
| 反応物 | Water | HCID 962 | — |
| 反応物 | Cesium carbonate | HCID 10796 | — |
| 反応物 | Phenylboronic Acid | HCID 66827 | — |
| 反応物 | 4-[2-(tert-butoxycarbonylamino)ethoxy]-N-(3-iodophenyl)-3-methoxyphenylacetamide | HCID 22019609 | — |
| 触媒 | HCID 178418397 | HCID 178418397 | — |
| 溶媒 | Tetrahydrofuran | HCID 8028 | — |
| 生成物 | 4-[2-(tert-butoxycarbonylamino)ethoxy]-3-methoxy-N-(3-phenylphenyl)phenylacetamide | HCID 22019616 | 77.3% |
反応手順
Intermediate 4 (500 mg) is dissolved in tetrahydrofuran (10 ml), and thereto are added tetrakis(triphenylphosphine)palladium (0) (110 mg), phenylboronic acid (230 mg), cesium carbonate (1.2 g) and water (2 ml), and the mixture is heated under reflux for 18 hours under argon atmosphere. The solvent is evaporated under reduced pressure, and the residue is purified by silica gel column chromatography (eluent: gradient from 0% to 100% hexane/ethyl acetate) to give 4-[2-(tert-butoxycarbonylamino)ethoxy]-3-methoxy-N-(3-phenylphenyl)phenylacetamide (350 mg). This product is treated with 10% hydrogen chloride-methanol to give the desired compound (210 mg).
情報源と証拠
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| 特許番号 | US07084176B2 |
| 出典データセット | uspto-grants-2006_08 |
| ORD ID | ord-8de8a8b5aa88425d8b13bde934774592 |
| 出典メモ | uspto-grants-2006_08 |