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Triethylamine → (S)-2-tert-Butoxycarbonylamino-3-[4-(pyridin-4-yloxy)-phenyl]-propionic acid methyl ester
関与物質
| 役割 | 名称 | HCID | 仕込み量 |
|---|---|---|---|
| 反応物 | Triethylamine | HCID 8471 | — |
| 反応物 | (Pyridin-4-yl)boronic acid | HCID 2734379 | — |
| 反応物 | Boc-Tyr-OMe | HCID 7019130 | — |
| 触媒 | Cupric acetate | HCID 8895 | — |
| 溶媒 | Dichloromethane | HCID 6344 | — |
| 溶媒 | Ethyl Acetate | HCID 8857 | — |
| 生成物 | (S)-2-tert-Butoxycarbonylamino-3-[4-(pyridin-4-yloxy)-phenyl]-propionic acid methyl ester | HCID 66922737 | 20.7% |
反応手順
(S)-2-tert-Butoxycarbonylamino-3-(4-hydroxy-phenyl)-propionic acid methyl ester (8.46 mmol), 4-pyridyl boronic acid (29.6 mmol), Cu(OAc)2 (16.9 mmol), and molecular sieves were suspended in 25 mL of DCM. Triethylamine (59.2 mmol) was added and the mixture stirred at rt for 10 h. The mixture was diluted with ethyl acetate and washed with 10% sodium carbonate (6×). The organic layer was dried and concentrated under reduced pressure. The residue was purified over silica gel (hexanes-EtOAc) to provide (S)-2-tert-Butoxycarbonylamino-3-[4-(pyridin-4-yloxy)-phenyl]-propionic acid methyl ester (653 mg). LC-MS (m/z) 374.
情報源と証拠
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| 特許番号 | US07727983B2 |
| 出典データセット | uspto-grants-2010_06 |
| ORD ID | ord-1cad58ca94e541a28a7f5dd0fffe7af6 |
| 出典メモ | uspto-grants-2010_06 |