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【结 构 式】 
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【分子编号】16496 【品名】4-[(2,2,2-trifluoroacetyl)oxy]benzoic acid 【CA登记号】 |
【 分 子 式 】C9H5F3O4 【 分 子 量 】234.1315096 【元素组成】C 46.17% H 2.15% F 24.34% O 27.33% |
合成路线1
该中间体在本合成路线中的序号：(VI)The condensation of adenine (I) with ethyl acrylate (II) by means of sodium ethoxide in methanol gives 3-(9-adenyl)propionic acid ethyl ester (III), which is treated with NaNO2/acetic acid yielding 3-(6-oxo-1,6-dihydro-9H-purin-9-yl)propionic acid ethyl ester (IV). The hydrolysis of (IV) with KOH in water affords the corresponding free acid (V), which is esterified with 4-chlorophenyl trifluoroacetate (VI) in pyridine giving the expected 4-chlorophenyl ester (VII). The condensation of ester (VII) with ethyl 4-aminobenzoate (VIII) by heating (35-40 C) in DMSO yields 4-[3-(6-oxo-1,6-dihydro-9H-purin-9-yl)propionamido]benzoic acid ethyl ester (IX), which is finally hydrolyzed with KOH in water.
| 【1】 Graul, A.; Castañer, J.; AIT-082. Drugs Fut 1997, 22, 9, 945. |
| 【2】 Glasky, A.J.; Multi-functional pharmaceutical cpds. and methods of use. WO 9114434 . |
| 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) | 10343 | 9H-Purin-6-amine; 9H-Purin-6-ylamine; Adenine | 73-24-5 | C5H5N5 | 详情 | 详情 |
| (II) | 10164 | ethyl acrylate | 140-88-5 | C5H8O2 | 详情 | 详情 |
| (III) | 16493 | ethyl 3-(6-amino-9H-purin-9-yl)propanoate | C10H13N5O2 | 详情 | 详情 | |
| (IV) | 16494 | ethyl 3-(6-oxo-1,6-dihydro-9H-purin-9-yl)propanoate | C10H12N4O3 | 详情 | 详情 | |
| (V) | 16495 | 3-(6-oxo-1,6-dihydro-9H-purin-9-yl)propionic acid | C8H8N4O3 | 详情 | 详情 | |
| (VI) | 16496 | 4-[(2,2,2-trifluoroacetyl)oxy]benzoic acid | C9H5F3O4 | 详情 | 详情 | |
| (VII) | 16497 | 4-[[3-(6-oxo-1,6-dihydro-9H-purin-9-yl)propanoyl]oxy]benzoic acid | C15H12N4O5 | 详情 | 详情 | |
| (VIII) | 16498 | Benzocaine; ethyl 4-aminobenzoate | 94-09-7 | C9H11NO2 | 详情 | 详情 |
| (IX) | 16499 | ethyl 4-[[3-(6-oxo-1,6-dihydro-9H-purin-9-yl)propanoyl]amino]benzoate | C17H17N5O4 | 详情 | 详情 |