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【结 构 式】 
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【分子编号】19836 【品名】methyl 2-[[2-(benzyloxy)benzoyl]amino]-3-hydroxybenzoate 【CA登记号】 |
【 分 子 式 】C22H19NO5 【 分 子 量 】377.3966 【元素组成】C 70.02% H 5.07% N 3.71% O 21.2% |
合成路线1
该中间体在本合成路线中的序号：(III)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 |