ethyl 2-[(4'-hydroxy[1,1'-biphenyl]-4-yl)oxy]acetate -Drug Synthesis Database

【结构式】

【分子编号】55987

【品名】ethyl 2-[(4'-hydroxy[1,1'-biphenyl]-4-yl)oxy]acetate

【CA登记号】

【分子式】C₁₆H₁₆O₄

【分子量】272.30064

【元素组成】C 70.57% H 5.92% O 23.5%

与该中间体有关的原料药合成路线共 2 条

合成路线1 合成路线2

合成路线1

该中间体在本合成路线中的序号：(III)

The alkylation of 4,4'-dihydroxybiphenyl (I) with ethyl bromoacetate (II) in the presence of sodium methoxide afforded the (biphenylyloxy)acetate (III). Heating of ester (III) with benzylamine (IV) at 85 C produced amide (V), which was subsequently reduced to amine (VI) by means of borane, generated in situ from NaBH4 and BF3. Finally, condensation of the secondary amine (VI) with methyl isocyanate gave rise to the title urea derivative.

参考文献中间体

合成目标

【1】 Fex, T.; Asp, B.; Stamvik, A.; Carlsson, J.-I.; Billstrom, A. (Pharmacia AB); Novel antitumour cpds. with antimitotic activity. WO 9529155 .

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)	55986	4,4'-Biphenol; 4,4'-Dihydroxybiphenyl; 4,4'-Dihydroxydiphenyl; 4,4'-Diphenol	92-88-6	C₁₂H₁₀O₂	详情	详情
(II)	16640	Ethyl 2-bromoacetate; Ethyl bromoacetate	105-36-2	C₄H₇BrO₂	详情	详情
(III)	55987	ethyl 2-[(4'-hydroxy[1,1'-biphenyl]-4-yl)oxy]acetate		C₁₆H₁₆O₄	详情	详情
(IV)	15147	Benzylamine; Phenylmethanamine	100-46-9	C₇H₉N	详情	详情
(V)	55988	N-benzyl-2-[(4'-hydroxy[1,1'-biphenyl]-4-yl)oxy]acetamide		C₂₁H₁₉NO₃	详情	详情
(VI)	55989	4'-[2-(benzylamino)ethoxy][1,1'-biphenyl]-4-ol		C₂₁H₂₁NO₂	详情	详情

合成路线2

该中间体在本合成路线中的序号：(III)

The alkylation of 4,4'-dihydroxybiphenyl (I) with ethyl bromoacetate (II) in the presence of sodium methoxide afforded the (biphenylyloxy)acetate (III). Heating of ester (III) with m-fluorobenzylamine (IV) at 85 C produced amide (V), which was subsequently reduced to amine (VI) by means of borane, generated in situ from NaBH4 and BF3. Finally, condensation of the secondary amine (VI) with methyl isocyanate gave rise to the title urea derivative.

参考文献中间体

合成目标

【1】 Fex, T.; Asp, B.; Stamvik, A.; Carlsson, J.-I.; Billstrom, A. (Pharmacia AB); Novel antitumour cpds. with antimitotic activity. WO 9529155 .

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)	55986	4,4'-Biphenol; 4,4'-Dihydroxybiphenyl; 4,4'-Dihydroxydiphenyl; 4,4'-Diphenol	92-88-6	C₁₂H₁₀O₂	详情	详情
(II)	16640	Ethyl 2-bromoacetate; Ethyl bromoacetate	105-36-2	C₄H₇BrO₂	详情	详情
(III)	55987	ethyl 2-[(4'-hydroxy[1,1'-biphenyl]-4-yl)oxy]acetate		C₁₆H₁₆O₄	详情	详情
(IV)	48834	3-Fluorobenzylamine	100-82-3	C₇H₈FN	详情	详情
(V)	55990	N-(3-fluorobenzyl)-2-[(4'-hydroxy[1,1'-biphenyl]-4-yl)oxy]acetamide		C₂₁H₁₈FNO₃	详情	详情
(VI)	55991	4'-{2-[(3-fluorobenzyl)amino]ethoxy}[1,1'-biphenyl]-4-ol		C₂₁H₂₀FNO₂	详情	详情

Extended Information