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【结 构 式】

【药物名称】Betaxolol hydrochloride, MCI-144, SL-75212, Betoptima, Kerlong, Betoptic, Kerlone

【化学名称】(±)-1-[4-[2-(Cyclopropylmethoxy)ethyl]phenoxy]-3-(isopropylamino)-2-propanol hydrochloride

【CA登记号】63659-19-8, 63659-18-7 (free base)

【 分 子 式 】C18H30ClNO3

【 分 子 量 】343.8977

【开发单位】Alcon (Originator), Mitsubishi Pharma (Not Determined), Sanofi-synthélabo (Licensee)

【药理作用】Angina pectoris, Treatment of, Antiglaucoma Agents, CARDIOVASCULAR DRUGS, Hypertension, Treatment of, OCULAR MEDICATIONS, Ophthalmic Drugs, Treatment of Disorders of the Coronary Arteries and Atherosclerosis, beta1-Adrenoceptor Antagonists

合成路线1

The condensation of ethyl p-hydroxyphenylacetate (I) with benzyl chloride (II) by means of sodium ethoxide in refluxing ethanol gives ethyl p-(benzyloxy)phenylacetate (III), which is reduced with LiAlH4 in THF to 2-(p-benzyloxyphenyl)ethanol (IV). The etherification of (IV) with cyclopropyl bromide (A) by means of NaH in hot DMF affords 4-(cyclopropylmethoxyethyl)-1-benzyloxybenzene (V), which is debenzylated by hydrogenation with H2 and Pd/C in methanol giving rise to p-(cyclopropylmethoxyethyl)phenol (VI). The condensation of (VI) with epichlorohydrin (B) by means of NaOH in water yields 1-[p-(cyclopropylmethoxyethyl)phenoxy]-2,3-epoxypropane (VII), which is treated with isopropylamine (C) and finally with HCl in ether.

1 Manoury, P.M.J.; et al. (Sanofi-Synthelabo ); Phenol ethers. DE 2649605; FR 2330383; GB 1515978; JP 52085146; US 4252984 .
2 Hillier, K.; Castaner, J.; Serradell, M.N.; Blancafort, P.; Betaxolol hydrochloride. Drugs Fut 1979, 4, 12, 867.
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(B) 10146 Epichlorohydrin; 2-(Chloromethyl)oxirane 106-89-8 C3H5ClO 详情 详情
(A) 22277 Cyclopropyl bromide; 1-(Bromomethyl)cyclopropane 7051-34-5 C4H7Br 详情 详情
(I) 24994 Ethyl 2-(4-hydroxyphenyl)acetate 17138-28-2 C10H12O3 详情 详情
(II) 19171 1-(Chloromethyl)benzene; Benzyl chloride 100-44-7 C7H7Cl 详情 详情
(III) 28637 Ethyl 2-[4-(benzyloxy)phenyl]acetate; p-(Benzyloxy)phenylacetate C17H18O3 详情 详情
(IV) 33328 2-(p-Benzyloxyphenyl)ethanol; 2-[4-(Benzyloxy)phenyl]-1-ethanol C15H16O2 详情 详情
(V) 33329 4-(Cyclopropylmethoxyethyl)-1-benzyloxybenzene; 1-(Benzyloxy)-4-[2-(cyclopropylmethoxy)ethyl]benzene; Benzyl 4-[2-(cyclopropylmethoxy)ethyl]phenyl ether C19H22O2 详情 详情
(VI) 33330 4-[2-(Cyclopropylmethoxy)ethyl]phenol; p-(Cyclopropylmethoxyethyl)phenol C12H16O2 详情 详情
(VII) 33331 2-([4-[2-(Cyclopropylmethoxy)ethyl]phenoxy]methyl)oxirane; 1-[p-(Cyclopropylmethoxyethyl)phenoxy]-2,3-epoxypropane; 4-[2-(Cyclopropylmethoxy)ethyl]phenyl 2-oxiranylmethyl ether C15H20O3 详情 详情
(C) 23933 2-Propanamine; Isopropylamine 75-31-0 C3H9N 详情 详情
Extended Information