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【结 构 式】 
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【分子编号】32700 【品名】4-[[(Z)-(4-chlorophenyl)(5-fluoro-2-hydroxyphenyl)methylidene]amino]butyric acid 【CA登记号】 |
【 分 子 式 】C17H15ClFNO3 【 分 子 量 】335.7621432 【元素组成】C 60.81% H 4.5% Cl 10.56% F 5.66% N 4.17% O 14.3% |
合成路线1
该中间体在本合成路线中的序号：(VII)The reaction of p-chlorobenzoic acid (I) with SOCl2 gives p-chlorobenzoyl chloride (II), which is esterified with 4-fluorophenol (III) affording 4-fluorophenyl-4-chlorobenzoate (IV). The isomerization of (IV) with AlCl3 yields 4-chloro-2'-hydroxy-5'-fluorobenzophenone (V), which is condensed with 4-aminobutyric acid (VI) by means of sodium methoxide in ethanol giving 4-[[alpha-(p-chlorophenyl)-5-fluoro-2-hydroxybenzylidene]amino]butyric acid (VII). The reaction of (VII) with SOCl2 in THF affords the corresponding acyl chloride (VIII), which is then treated with NH3. An alternative way of converting the acid (VII) into its amide is by treatment with carbonyldiimidazole (A) and liquid NH3 in THF.
| 【1】 Kaplan, J.P.; et al.; Derives alpha-phenyl-benzylideniques des acides amines. FR 2358887 . |
| 【2】 Kaplan, J.P.; et al. (Sanofi-Synthelabo); Benzylidene derivatives. ES 450300; FR 2319338; GB 1506808; JP 52019644; US 4094992 . |
| 【3】 Kaplan, J.P.; et al. (Sanofi-Synthelabo); Preparation of benzylidene derivatives. DE 2830034; ES 471606; FR 2397397; GB 2001066; JP 54019953 . |
| 【4】 Serradell, M.N.; Owen, R.T.; Blancafort, P.; Castaner, J.; Progabide. Drugs Fut 1980, 5, 9, 445. |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (A) | 11353 | 1,1'-Carbonyldiimidazole; Di(1H-imidazol-1-yl)methanone; N,N-Carbonyldiimidazole; 1,1'-Carbonylbis(1H-imidazole) | 530-62-1 | C7H6N4O | 详情 | 详情 |
| (I) | 18359 | p-chlorobenzoic acid; 4-chlorobenzoic acid | 74-11-3 | C7H5ClO2 | 详情 | 详情 |
| (II) | 10295 | p-Chlorobenzoyl chloride; 4-Chlorobenzoyl chloride | 122-01-0 | C7H4Cl2O | 详情 | 详情 |
| (III) | 19639 | 4-fluorophenol | 371-41-5 | C6H5FO | 详情 | 详情 |
| (IV) | 32698 | 4-Fluorophenyl 4-chlorobenzoate | C13H8ClFO2 | 详情 | 详情 | |
| (V) | 32699 | (4-chlorophenyl)(5-fluoro-2-hydroxyphenyl)methanone | 62433-26-5 | C13H8ClFO2 | 详情 | 详情 |
| (VI) | 13620 | 4-Amino-n-butyric acid; 4-Aminobutyric acid;Piperidinic acid;Piperidic acid | 56-12-2 | C4H9NO2 | 详情 | 详情 |
| (VII) | 32700 | 4-[[(Z)-(4-chlorophenyl)(5-fluoro-2-hydroxyphenyl)methylidene]amino]butyric acid | C17H15ClFNO3 | 详情 | 详情 | |
| (VIII) | 32701 | 4-[[(Z)-(4-chlorophenyl)(5-fluoro-2-hydroxyphenyl)methylidene]amino]butanoyl chloride | C17H14Cl2FNO2 | 详情 | 详情 |