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【结 构 式】 
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【分子编号】66054 【品名】2,2,2-Trifluoro-N-(4-Mercaptophenyl)Acetamide; 2,2,2-Trifluoro-N-(4-Sulfanylphenyl)Ethanamide 【CA登记号】94006-35-6 |
【 分 子 式 】C8H6F3NOS 【 分 子 量 】221.2029896 【元素组成】C 43.44% H 2.73% F 25.77% N 6.33% O 7.23% S 14.5% |
合成路线1
该中间体在本合成路线中的序号：(XXI)Synthesis of intermediate (VII):
Reaction of 4-sulfanylaniline (XX) with TFAA in the presence of Et3N in THF gives trifluoroacetamide (XXI), which then condenses with 5-(chloromethyl)-1-propylimidazole (V) using TEA in MeOH/H2O to yield thioether (XXII). Oxidation of sulfanyl derivative (XXII) by means of H2O2 in AcOH, followed by hydrolysis with NaOH affords the racemic sulfinyl derivative (XXIII), which is then submitted to optical resolution with di-p-toluoyl-D-tartaric acid to provide the desired (S)-enantiomer (VII) (1). Scheme 3.
| 【1】 Nishiguchi, A., Adachi, M., Ito, T., Ikemoto, T., Tawada, H. (Takeda Pharmaeutical Co., Ltd.). Process for producing optically active sulfoxide derivative. CA 2479071, EP 1484322, JP 2004123694, WO 2003076411. |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (V) | 66041 | 5-(chloromethyl)-1-propylimidazole | C7H11ClN2 | 详情 | 详情 | |
| (VII) | 66043 | C13H17N3OS | 详情 | 详情 | ||
| (XX) | 16490 | 4-aminophenylhydrosulfide; 4-aminothiophenol; 4-aminobenzenethiol | 1193-02-8 | C6H7NS | 详情 | 详情 |
| (XXI) | 66054 | 2,2,2-Trifluoro-N-(4-Mercaptophenyl)Acetamide; 2,2,2-Trifluoro-N-(4-Sulfanylphenyl)Ethanamide | 94006-35-6 | C8H6F3NOS | 详情 | 详情 |
| (XXII) | 66055 | C15H16F3N3OS | 详情 | 详情 | ||
| (XXIII) | 66056 | C13H17N3OS | 详情 | 详情 |