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【结 构 式】

【分子编号】19835

【品名】2-(benzyloxy)benzoyl chloride

【CA登记号】

【 分 子 式 】C14H11ClO2

【 分 子 量 】246.69284

【元素组成】C 68.16% H 4.49% Cl 14.37% O 12.97%

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:(II)

The reaction of 2-amino-3-hydroxy benzoic acid methyl ester (I) with 2-benzyloxybenzoyl chloride (II) by means of pyridine in benzene gives the corresponding amide (III), which is cyclized by heating at 230 C yielding 2-(benzyloxyphenyl)benzoxazole-4-carboxylic acid methyl ester (IV). The hydrolysis of (IV) by means of NaOH in THF/water affords the correponding free acid (V), which is condensed with 2-amino-3-hydroxybenzoic acid methyl ester (I) by means of oxalyl chloride to give the expected amide (VI). Finally, this compound is cyclized by means of p-toluenesulfonic acid in refluxing toluene.

1 Kerwin, S.M.; et al.; The novel bis(benzoxazole) cytotoxic natural product UK-1 is a magnesium ion-dependent DNA binding agent and inhibitor of human topoisomerase II. 213th ACS Natl Meet (April 13-17, San Francisco) 1997, Abst MEDI 216.
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) 19834 methyl 2-amino-3-hydroxybenzoate C8H9NO3 详情 详情
(II) 19835 2-(benzyloxy)benzoyl chloride C14H11ClO2 详情 详情
(III) 19836 methyl 2-[[2-(benzyloxy)benzoyl]amino]-3-hydroxybenzoate C22H19NO5 详情 详情
(IV) 19837 methyl 2-[2-(benzyloxy)phenyl]-1,3-benzoxazole-4-carboxylate C22H17NO4 详情 详情
(V) 19838 2-[2-(benzyloxy)phenyl]-1,3-benzoxazole-4-carboxylic acid C21H15NO4 详情 详情
(VI) 19839 methyl 2-[([2-[2-(benzyloxy)phenyl]-1,3-benzoxazol-4-yl]carbonyl)amino]-3-hydroxybenzoate C29H22N2O6 详情 详情
(IX) 16593 Phenylboronic acid;Benzeneboronic acid;Phenylboron dihydroxide 98-80-6 C6H7BO2 详情 详情
Extended Information