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【结 构 式】

【分子编号】13667

【品名】2,2,2-trichloroethyl (5-[[(2-aminoethyl)sulfanyl]methyl]-2-furyl)methyl(methyl)carbamate

【CA登记号】

【 分 子 式 】C12H17Cl3N2O3S

【 分 子 量 】375.70276

【元素组成】C 38.36% H 4.56% Cl 28.31% N 7.46% O 12.78% S 8.53%

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:(V)

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
Extended Information