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【结 构 式】

【分子编号】13899

【品名】methyl 5-chloro-2-hydroxy-3-(2-methyl-2-propenyl)benzoate

【CA登记号】

【 分 子 式 】C12H13ClO3

【 分 子 量 】240.68612

【元素组成】C 59.88% H 5.44% Cl 14.73% O 19.94%

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)

1) The esterification of 5-chloro-2-hydroxybenzoic acid (I) with methanol - HCl gives the corresponding methyl ester (II), which is alkylated with 3-chloro-2-methylpropene (III) to afford methyl 5-chloro-2-(2-methyl-2-propenyloxy)benzoate (IV). The rearrangement of (IV) by heating with N-methylpyrrolidine yields methyl 5-chloro-2-hydroxy-3-(2-methyl-2-propenyl)benzoate (V). The cyclization of (V) in formic acid followed by hydrolysis with NaOH gives 5-chloro-2,2-dimethyl-2,3-dihydrobenzofuran-7-carboxylic acid (VI), which is finally treated with SOCl2, condensed with 3alpha-aminotropane (VII) and treated with maleic acid.

1 Cohen, M.L.; Lacefield, W.B. (Eli Lilly and Company); Improvements in or relating to specific 5-HT3 antagonists. AU 8821916; EP 0307172; JP 1989110684 .
2 Robertson, D.W.; Bloomquist, W.; Pfiefer, W.; Cohen, M.L.; Simon, R.L.; Lacefield, W.B.; Zatosetron, a potent, selective, and long-acting 5-HT3 receptor antagonist: Synthesis and structure-activity relationships. J Med Chem 1992, 35, 2, 310-9.
3 Graul, A.; Castaner, J.; Prous, J.; Zatosetron Maleate. Drugs Fut 1994, 19, 9, 850.
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) 13895 5-Chloro-2-hydroxybenzoic acid; 5-Chlorosalicylic acid 321-14-2 C7H5ClO3 详情 详情
(II) 13714 Methyl 5-chloro-2-hydroxybenzoate; Methyl 5-chlorosalicylate 4068-78-4 C8H7ClO3 详情 详情
(III) 12127 3-Chloro-2-methyl-1-propene; Isobutenyl chloride 563-47-3 C4H7Cl 详情 详情
(IV) 13898 methyl 5-chloro-2-[(2-methyl-2-propenyl)oxy]benzoate C12H13ClO3 详情 详情
(V) 13899 methyl 5-chloro-2-hydroxy-3-(2-methyl-2-propenyl)benzoate C12H13ClO3 详情 详情
(VI) 13900 5-Chloro-2,2-dimethyl-2,3-dihydro-1-benzofuran-7-carboxylic acid C11H11ClO3 详情 详情
(VII) 12412 (1R,5S)-8-Methyl-8-azabicyclo[3.2.1]octan-3-amine; (1R,5S)-8-Methyl-8-azabicyclo[3.2.1]oct-3-ylamine C8H16N2 详情 详情
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