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【结 构 式】 
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【分子编号】29750 【品名】ethyl (2R)-4-(2-amino-6-chloro-9H-purin-9-yl)-2-hydroxybutanoate 【CA登记号】 |
【 分 子 式 】C11H14ClN5O3 【 分 子 量 】299.71676 【元素组成】C 44.08% H 4.71% Cl 11.83% N 23.37% O 16.01% |
与该中间体有关的原料药合成路线共 1 条
合成路线1
该中间体在本合成路线中的序号：(III)The condensation of 2-amino-6-chloropurine (I) with ethyl 4-bromo-2-hydroxybutyrate (II) by means of K2CO3 in DMF gives ethyl 4-(2-amino-6-chloropurin-9-yl)-2-hydroxybutyrate (III), which 8-hydrolyzed with refluxing aqueous HCl yielding 4-(9-guanyl)-2-hydroxybutyric acid (IV). The esterification of (IV) with ethanol - HCl affords the corresponding ethyl ester (V), which is finally reduced with NaBH4 in refluxing isopropanol.
| 【1】 Johansson, N.G.; Datema, R.; Ericson, A.C.; Lindborg, B.; Oberg, B.; Larsson, A.; Stening, G.; Eklind, K.; Kovocs, S.; Hagberg, C.E.; The synthesis and antiherpetic activity of DHBG and some analogs. Nucleosides Nucleotides 1985, 4, 1&2, 303. |
| 【2】 Hagberg, C.-E.; et al. (AstraZeneca AB); Derivatives of guanine for combating herpes virus infections. EP 0055239; US 4495190; WO 8202202 . |
| 【3】 Serradell, M.N.; Hopkins, S.J.; Castaner, J.; Buciclovir. Drugs Fut 1985, 10, 11, 894. |
| 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) | 11644 | 6-Chloro-9H-purin-2-amine; 6-Chloro-9H-purin-2-ylamine; 2-Amino-6-chloropurine | 10310-21-1 | C5H4ClN5 | 详情 | 详情 |
| (II) | 29749 | ethyl (2R)-4-bromo-2-hydroxybutanoate | C6H11BrO3 | 详情 | 详情 | |
| (III) | 29750 | ethyl (2R)-4-(2-amino-6-chloro-9H-purin-9-yl)-2-hydroxybutanoate | C11H14ClN5O3 | 详情 | 详情 | |
| (IV) | 29751 | (2R)-4-(2-amino-6-oxo-1,6-dihydro-9H-purin-9-yl)-2-hydroxybutyric acid | C9H11N5O4 | 详情 | 详情 | |
| (V) | 29752 | ethyl (2R)-4-(2-amino-6-oxo-1,6-dihydro-9H-purin-9-yl)-2-hydroxybutanoate | C11H15N5O4 | 详情 | 详情 |
Extended Information