methyl 2-[([2-[2-(benzyloxy)phenyl]-1,3-benzoxazol-4-yl]carbonyl)amino]-3-hydroxybenzoate -Drug Synthesis Database

【结构式】

【分子编号】19839

【品名】methyl 2-[([2-[2-(benzyloxy)phenyl]-1,3-benzoxazol-4-yl]carbonyl)amino]-3-hydroxybenzoate

【CA登记号】

【分子式】C₂₉H₂₂N₂O₆

【分子量】494.50356

【元素组成】C 70.44% H 4.48% N 5.66% O 19.41%

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：(VI)

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.

参考文献中间体

合成目标

【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