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【结 构 式】

【分子编号】39965

【品名】2-hydroxyethyl benzoate

【CA登记号】

【 分 子 式 】C9H10O3

【 分 子 量 】166.1766

【元素组成】C 65.05% H 6.07% O 28.88%

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 reaction of benzonitrile (I) with refluxing ethylene glycol (II) gives ethylene glycol monobenzoate (III), which is chloromethylated with formaldehyde and dry HCl in CH2Cl2 affording 1-benzoyloxy-2-chloromethoxyethane (IV). The condensation of (IV) with 2,6-dichloropurine (V) by means of triethylamine in DMF yields 2,6-dichloro-9-(2-benzoyloxyethoxymethyl)purine (VI), which is aminated and debenzoylated by treatment with NH3 in methanol at 95 C in a pressure vessel giving 2-chloro-9-(2-hydroxyethoxymethyl)adenine (VII). The Sandmeyer reaction of (VII) with NaNO2 in acetic acid affords 2-chloro-9-(2-hydroxyethoxymethyl)hypoxanthine (VIII), which is finally amonolyzed with ammonia in methanol at 125 C in a pressure vessel.

1 Schaeffer, H.J.; et al.; 9-(2-Hydroxyethoxy)guanine activity aganist viruses of the herpes group. Nature 1978, 272, 583-585.
2 Castaner, J.; Hillier, K.; Acycloguanosine. Drugs Fut 1978, 3, 11, 788.
3 Schaeffer, H.J. (Glaxo Wellcome plc); Purine derivs.. US 4294831 .
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) 25904 benzonitrile 100-47-0 C7H5N 详情 详情
(II) 11295 Polyethylene glycol;1,2-Ethanediol;Monoethylene glycol; Ethylene glycol 107-21-1 C2H6O2 详情 详情
(III) 39965 2-hydroxyethyl benzoate C9H10O3 详情 详情
(IV) 39966 2-(chloromethoxy)ethyl benzoate C10H11ClO3 详情 详情
(V) 25254 2,6-dichloro-9H-purine 5451-40-1 C5H2Cl2N4 详情 详情
(VI) 39967 2-[(2,6-dichloro-9H-purin-9-yl)methoxy]ethyl benzoate C15H12Cl2N4O3 详情 详情
(VII) 39968 2-[(6-amino-2-chloro-9H-purin-9-yl)methoxy]-1-ethanol C8H10ClN5O2 详情 详情
(VIII) 39969 2-chloro-9-[(2-hydroxyethoxy)methyl]-9H-purin-6-ol C8H9ClN4O3 详情 详情
Extended Information