참여 물질
| 역할 | 이름 | HCID | 투입량 |
|---|
| 반응물 | Hydrochloric Acid | HCID 313 | — |
| 반응물 | L-Alanine | HCID 5950 | — |
| 반응물 | Potassium Phosphate, Tribasic | HCID 62657 | — |
| 반응물 | Benzene, 1,2-dichloro-4-iodo- | HCID 88591 | — |
| 반응물 | 2-Hydroxybenzaldehyde phenylhydrazone | HCID 249842 | — |
| 촉매 | Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI) | HCID 24350 | — |
| 용매 | Water | HCID 962 | — |
| 용매 | Dimethylformamide | HCID 6228 | — |
| 생성물 | 2-(3,4-Dichloro-phenylamino)-propionic Acid | HCID 6916426 | 83.9% |
반응 단계
A mixture of 3,4-dichloroiodobenzene (1.50 g, 5.50 mmol), L-alanine (734 mg, 8.25 mmol), copper(I) iodide, 2-hydroxybenzaldehyde phenylhydrazone (233 mg, 1.10 mmol), tri-potassium phosphate (3.50 g, 16.5 mmol), and N,N-dimethylformamide (8 mL) was stirred at 80° C. for 40 h, then after cooling diluted with water and acidified to pH 3 by addition of 37% aq. HCl solution. The mixture was extracted with EtOAc, the organic phase was washed with brine, dried (MgSO4), filtered, and evaporated. Chromatography (SiO2; EtOAc) afforded the title compound (1.08 g, 67%) as a 71:29 mixture of the (S) and (R) stereoisomers (accordingly, when D-alanine was used instead of L-alanine as starting material, the title compound was obtained as a 29:71 mixture of the (S) and (R) stereoisomers). Brown solid, MS: 232.1 (M−H)−.
출처 및 근거
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| 특허 번호 | US08138175B2 |
|---|
| 출처 데이터셋 | uspto-grants-2012_03 |
|---|
| ORD ID | ord-ba18df7b02184cea8a743c632e8b5caf |
|---|
| 출처 메모 | uspto-grants-2012_03 |
|---|
