関与物質
| 役割 | 名称 | HCID | 仕込み量 |
|---|
| 反応物 | Hydrochloric Acid | HCID 313 | — |
| 反応物 | Potassium Phosphate, Tribasic | HCID 62657 | — |
| 反応物 | D-Alanine | HCID 71080 | — |
| 反応物 | Benzene, 1,2-dichloro-4-iodo- | HCID 88591 | — |
| 反応物 | 2-Hydroxybenzaldehyde phenylhydrazone | HCID 249842 | — |
| 触媒 | Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI) | HCID 24350 | — |
| 溶媒 | Water | HCID 962 | — |
| 溶媒 | Dimethylformamide | HCID 6228 | — |
| 生成物 | (R)-2-(3,4-Dichloro-phenylamino)-propionic acid | HCID 182146 | 60.4% |
反応手順
A mixture of 6.00 g (22.00 mmol) 3,4-dichloroiodobenzene, 2.94 g (33.00 mmol) D-alanine, 0.42 g (2.20 mmol) copper(I) iodide, 0.96 g (4.40 mmol) 2-hydroxybenzaldehyde phenylhydrazone, 14.00 g (66.00 mmol) tri-potassium phosphate in 32 ml of N,N-dimethylformamide was stirred at 80° C. for 16 h under argon, then after cooling diluted with water and acidified to pH 3 by addition of 25% aq. HCl solution. The mixture was extracted with EtOAc (3×), the organic phases were washed with brine, dried (Na2SO4), filtered and evaporated. Flash chromatography (SiO2; dichloromethane/MeOH 95:5 to 4:1) afforded 3.11 g (60%) of the title compound (as 81:19 mixture of the (R) and (S) stereoisomers, BGB-175*0.25 column) as light brown solid. MS: 231.9 (M−H−, 2Cl).
情報源と証拠
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| 特許番号 | US08445674B2 |
|---|
| 出典データセット | uspto-grants-2013_05 |
|---|
| ORD ID | ord-762c2d4777384a30afd91c16ba20d130 |
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| 出典メモ | uspto-grants-2013_05 |
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