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【结 构 式】 
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【分子编号】13669 【品名】4-(2-Amino-1-hydroxyethyl)phenol 【CA登记号】104-14-3 |
【 分 子 式 】C8H11NO2 【 分 子 量 】153.18088 【元素组成】C 62.73% H 7.24% N 9.14% O 20.89% |
合成路线1
该中间体在本合成路线中的序号：(VII)The acylation of 5-(methylaminomethyl)furan-2-methanol (I) with 2,2,2-trichloroethyl chloroformate (II) and pyridine in dichloromethane gives the corresponding N-acyl derivative (III), which is condensed with 2-mercaptoethylamine (IV) by means of sodium methoxide in methanol to yield the thioether (V). The condensation of (V) with diphenyl methanesulfonimidocarbonate (VI) and 2-hydroxy-2-(4-hydroxyphenyl)ethylamine (VII) by means of potassium acetate and triethylamine in acetonitrile - propanol affords the protected final product (VIII), which is finally deprotected by treatment with activated Zn and potassium dihydrogen phosphate.
| 【1】 Hirai, S.; Hirano, H.; Arai, H.; Shibata, H.; Kusayanagi, Y.; Hashiba, K. (Toyama Chemical Co., Ltd.); Amine deriv. and its salts and antiulcer agent containing the same. CH 675244; DE 3828869; US 4871765 . |
| 【2】 Castaner, J.; Prous, J.; Mealy, N.; T-593. Drugs Fut 1993, 18, 9, 809. |
| 【3】 Shibata, H.; Hirai, N.; Kusayanagi, K.; Arai, H.; Hirano, H.; Synthesis of beta-hydroxyphenethyl-based compounds and their physico-chemical properties and structural features. 113th Annu Meet Pharmaceut Soc Jpn (March 29-31, Osaka) 1993, Abst 29PB 10-28. |
| 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) | 13663 | [5-[(Methylamino)methyl]-2-furyl]methanol | C7H11NO2 | 详情 | 详情 | |
| (II) | 13664 | 1,1,1-Trichloro-2-[(chlorocarbonyl)oxy]ethane; 2,2,2-Trichloroethyl chloroformate | 17341-93-4 | C3H2Cl4O2 | 详情 | 详情 |
| (III) | 13665 | 2,2,2-trichloroethyl [5-(hydroxymethyl)-2-furyl]methyl(methyl)carbamate | C10H12Cl3NO4 | 详情 | 详情 | |
| (IV) | 13186 | 2-Aminoethanethiol; 2-Amino-1-ethanethiol; 2-Aminoethylhydrosulfide; Cysteamine | 60-23-1 | C2H7NS | 详情 | 详情 |
| (V) | 13667 | 2,2,2-trichloroethyl (5-[[(2-aminoethyl)sulfanyl]methyl]-2-furyl)methyl(methyl)carbamate | C12H17Cl3N2O3S | 详情 | 详情 | |
| (VI) | 13668 | N-(Diphenoxymethylene)methanesulfonamide | C14H13NO4S | 详情 | 详情 | |
| (VII) | 13669 | 4-(2-Amino-1-hydroxyethyl)phenol | 104-14-3 | C8H11NO2 | 详情 | 详情 |
| (VIII) | 13670 | 2,2,2-trichloroethyl [5-((E)-6-[[2-hydroxy-2-(4-hydroxyphenyl)ethyl]amino]-8,8-dioxo-2,8lambda(6)-dithia-5,7-diaza-6-nonen-1-yl)-2-furyl]methyl(methyl)carbamate | C22H29Cl3N4O7S2 | 详情 | 详情 |