関与物質
| 役割 | 名称 | HCID | 仕込み量 |
|---|
| 反応物 | Hydrochloric Acid | HCID 313 | — |
| 反応物 | L-Alanine | HCID 5950 | — |
| 反応物 | Potassium Carbonate | HCID 11430 | — |
| 反応物 | Iodobenzene | HCID 11575 | — |
| 触媒 | Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI) | HCID 24350 | — |
| 触媒 | Benzyl triethylammonium chloride | HCID 66133 | — |
| 触媒 | Bis(tri-o-tolylphosphine)palladium(II) Dichloride | HCID 10876480 | — |
| 溶媒 | Water | HCID 962 | — |
| 溶媒 | Dimethylformamide | HCID 6228 | — |
| 溶媒 | Triethylamine | HCID 8471 | — |
| 溶媒 | Ethyl Acetate | HCID 8857 | — |
| 溶媒 | Ethyl acetate hexane acetic acid | HCID 21901998 | — |
| 生成物 | 2-(Phenylamino)propanoic acid | HCID 2760357 | 45.4% |
反応手順
A mixture of alanine (356 mg, 4.0 mmol), iodobenzene (816 mg, 4.0 mmol), trans-dichlorobis(tri-o-tolylphosphine)palladium(II) {Pd[P(o-Tol)3]2Cl2} (160 mg, 0.2 mmol), copper(I) iodide (40 mg, 0.2 mmol), K2CO3 (552 mg, 4.0 mmol), benzyltriethylammonium chloride (160 mg, 0.8 mmol), triethylamine (1.6 mL) and water (0.8 mL) in DMF (8 mL) was stirred under nitrogen atmosphere at 100° C. for 20 hours. The mixture was cooled to room temperature, diluted with ethyl acetate (50 mL) and water (50 mL), acidified with 6N HCl to the pH=2 to 3. The aqueous layer was extracted with ethyl acetate (50 mL×4). The combined organic layers were washed with water, brine, dried over anhydrous Na2SO4, filtered and evaporated in vacuo to give a red oil. Flash chromatography using hexane/ethyl acetate/acetic acid (95/5/0.5 to 80/20/0.5) to afford 300 mg (45% yield) of the title compound as a pink solid. 1H-NMR (500 MHz, CDCl3/CD3OD=0.5 ml/3 drops) δ 1.45 (d, 3H), 4.02-4.15 (m, H), 6.57-6.70 (m, 3H), 7.11-7.25 (m, 2H); Analytical HPLC: 6.10 min. LC-MS: m/e=166 (M+H+).
情報源と証拠
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| 特許番号 | US07358273B2 |
|---|
| 出典データセット | uspto-grants-2008_04 |
|---|
| ORD ID | ord-f521e4f4c0254f28b604189a0262906d |
|---|
| 出典メモ | uspto-grants-2008_04 |
|---|
