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【结 构 式】 
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【分子编号】30400 【品名】tert-butyl (1S)-1-[4-(benzyloxy)benzyl]-2-(6-fluoro-2-oxo-2,3-dihydro-1H-benzimidazol-1-yl)-2-thioxoethylcarbamate 【CA登记号】 |
【 分 子 式 】C28H28FN3O4S 【 分 子 量 】521.6125432 【元素组成】C 64.47% H 5.41% F 3.64% N 8.06% O 12.27% S 6.15% |
合成路线1
该中间体在本合成路线中的序号：(V)Coupling of N-Boc-O-benzyltyrosine (I) with 4-fluoro-1,2-phenylenediamine (II) by means of EDC afforded amide (III), which was converted into thioamide (IV) upon treatment with phosphorus pentasulfide and Na2CO3. Then, ring closure of (IV) with phosgene afforded the benzimidazolone derivative (V).
| 【1】 Zackarie, B.; et al.; Thioamides: Synthesis, stability, and immunological activities of thioanalogues of imreg. Preparation Of new thioacylating agents using fluorobenzimidazolone derivatives. J Med Chem 1999, 42, 11, 2046. |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (I) | 30396 | (2S)-3-[4-(benzyloxy)phenyl]-2-[(tert-butoxycarbonyl)amino]propionic acid | 54784-43-9 | C21H25NO5 | 详情 | 详情 |
| (II) | 30397 | 2-amino-4-fluorophenylamine; 4-fluoro-1,2-benzenediamine | 367-31-7 | C6H7FN2 | 详情 | 详情 |
| (III) | 30398 | tert-butyl (1S)-2-(2-amino-5-fluoroanilino)-1-[4-(benzyloxy)benzyl]-2-oxoethylcarbamate | C27H30FN3O4 | 详情 | 详情 | |
| (IV) | 30399 | tert-butyl (1S)-2-(2-amino-5-fluoroanilino)-1-[4-(benzyloxy)benzyl]-2-thioxoethylcarbamate | C27H30FN3O3S | 详情 | 详情 | |
| (V) | 30400 | tert-butyl (1S)-1-[4-(benzyloxy)benzyl]-2-(6-fluoro-2-oxo-2,3-dihydro-1H-benzimidazol-1-yl)-2-thioxoethylcarbamate | C28H28FN3O4S | 详情 | 详情 |
合成路线2
该中间体在本合成路线中的序号：(V)Coupling of N-Boc-glycine (VI) with glycine benzyl ester hydrochloride (VII) by means of 2-ethoxy-1-ethoxycarbonyl-1,2-dihydroquinoline (EEDQ) gave the protected dipeptide (VIII). After deprotection of the Boc group of (VIII) with HCl, the resulting amine (IX) was condensed with the thioacylating compound (V) to furnish thioamide (X). Finally, the Boc and benzyl protecting groups of (X) were cleaved using HF.
| 【1】 Zackarie, B.; et al.; Thioamides: Synthesis, stability, and immunological activities of thioanalogues of imreg. Preparation Of new thioacylating agents using fluorobenzimidazolone derivatives. J Med Chem 1999, 42, 11, 2046. |
| 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) | 30400 | tert-butyl (1S)-1-[4-(benzyloxy)benzyl]-2-(6-fluoro-2-oxo-2,3-dihydro-1H-benzimidazol-1-yl)-2-thioxoethylcarbamate | C28H28FN3O4S | 详情 | 详情 | |
| (VI) | 18066 | N-alpha-t-BOC-glycine; 2-[(tert-butoxycarbonyl)amino]acetic acid | 4530-20-5 | C7H13NO4 | 详情 | 详情 |
| (VII) | 13601 | benzyl 2-aminoacetate; Glycine benzyl ester hydrochloride | 1738-68-7 | C9H11NO2 | 详情 | 详情 |
| (VIII) | 30401 | benzyl 2-([2-[(tert-butoxycarbonyl)amino]acetyl]amino)acetate | C16H22N2O5 | 详情 | 详情 | |
| (IX) | 30402 | benzyl 2-[(2-aminoacetyl)amino]acetate | C11H14N2O3 | 详情 | 详情 | |
| (X) | 30403 | benzyl (6S)-6-[4-(benzyloxy)benzyl]-2,2-dimethyl-4,10-dioxo-7-thioxo-3-oxa-5,8,11-triazatridecan-13-oate | C32H37N3O6S | 详情 | 详情 |