1-[4-(benzyloxy)-3-isocyanatophenyl]-1-ethanone -Drug Synthesis Database

【结构式】

【分子编号】60749

【品名】1-[4-(benzyloxy)-3-isocyanatophenyl]-1-ethanone

【CA登记号】

【分子式】C₁₆H₁₃NO₃

【分子量】267.28416

【元素组成】C 71.9% H 4.9% N 5.24% O 17.96%

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 3-amino-4-benzyloxyacetophenone (I) with phosgene in toluene gives 3-isocyanate-4-benzyloxyacetophenone (II), which by reaction with ammonia in benzene yields 4-benzyloxy-3-ureidoacetophenone (III). The bromination of this product with Br2 in CHCl3 affords 4-benzyloxy-3-ureidophenacyl bromide (IV), amorphous product that is condensed with N-benzyl-N-tert-butylamine (V) in acetonitrile giving 4-benzyloxy-3-ureido-alpha-(N-benzyl-N-tert-butylamine)acetophenone hydrochloride (VI), m.p. 220-1 C. This product is finally hydrogenated with H2 over Pd/C in methanol

参考文献中间体

合成目标

【1】 Castaner, J.; Sungurbey, K.; Carbuterol. Drugs Fut 1976, 1, 9, 412.
【2】 Kaiser C.; et al. (Smith Kline French); DE 2106620 .

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)	20628	1-[3-amino-4-(benzyloxy)phenyl]-1-ethanone		C₁₅H₁₅NO₂	详情	详情
(II)	60749	1-[4-(benzyloxy)-3-isocyanatophenyl]-1-ethanone		C₁₆H₁₃NO₃	详情	详情
(III)	60750	N-[5-acetyl-2-(benzyloxy)phenyl]urea		C₁₆H₁₆N₂O₃	详情	详情
(IV)	60751	N-[2-(benzyloxy)-5-(2-bromoacetyl)phenyl]urea hydrobromide		C₁₆H₁₆Br₂N₂O₃	详情	详情
(V)	24700	N-benzyl-2-methyl-2-propanamine	3378-72-1	C₁₁H₁₇N	详情	详情
(VI)	60752	N-[5-{2-[benzyl(tert-butyl)amino]acetyl}-2-(benzyloxy)phenyl]urea		C₂₇H₃₁N₃O₃	详情	详情

Extended Information