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【结 构 式】 
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【分子编号】50844 【品名】1-[2-[3-(tert-butylamino)-2-hydroxypropoxy]-5-nitrophenyl]-1-ethanone 【CA登记号】 |
【 分 子 式 】C15H22N2O5 【 分 子 量 】310.35016 【元素组成】C 58.05% H 7.15% N 9.03% O 25.78% |
合成路线1
该中间体在本合成路线中的序号：(VII)The reaction of 4-nitrophenol (I) with acetic anhydride in aqueous NaOH gives the corresponding acetate (II), which is submitted to a Fries migration with AlCl3 in nitrobenzene at 140 C to yield the acetophenone (III). The condensation of (III) with epichlorohydrin (IV) by means of K2CO3 affords the adduct (V), which is treated with tert-butylamine (VI) in water to obtain the aminoisopropanol derivative (VII). The reduction of the nitro group of (VII) with H2 over Pd/C in methanol gives the corresponding amino derivative (VIII), which is finally condensed with N,N-diethylcarbamoyl chloride (IX) by means of TEA in THF to yield the target urea.
| 【1】 Joshi, R.A.; et al.; A new and improved process for celiprolol hydrochloride. Org Process Res Dev 2001, 5, 2, 176. |
| 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) | 11236 | 4-Nitrophenol; p-Nitrophenol | 100-02-7 | C6H5NO3 | 详情 | 详情 |
| (II) | 50841 | 4-Nitrophenyl acetate; Acetic acid 4-nitrophenyl ester; p-Nitrophenyl acetate | 830-03-5 | C8H7NO4 | 详情 | 详情 |
| (III) | 50842 | 1-(2-hydroxy-5-nitrophenyl)-1-ethanone | C8H7NO4 | 详情 | 详情 | |
| (IV) | 10146 | Epichlorohydrin; 2-(Chloromethyl)oxirane | 106-89-8 | C3H5ClO | 详情 | 详情 |
| (V) | 50843 | 1-[5-nitro-2-(2-oxiranylmethoxy)phenyl]-1-ethanone | C11H11NO5 | 详情 | 详情 | |
| (VI) | 17895 | 2-Amino-2-methylpropane; tert-butylamine; 2-methyl-2-propanamine | 75-64-9 | C4H11N | 详情 | 详情 |
| (VII) | 50844 | 1-[2-[3-(tert-butylamino)-2-hydroxypropoxy]-5-nitrophenyl]-1-ethanone | C15H22N2O5 | 详情 | 详情 | |
| (VIII) | 33819 | 1-[5-amino-2-[3-(tert-butylamino)-2-hydroxypropoxy]phenyl]-1-ethanone | C15H24N2O3 | 详情 | 详情 | |
| (IX) | 33816 | N,N'-Diethylcarbamoyl chloride; 1-[(chlorocarbonyl)(ethyl)amino]ethane | 88-10-8 | C5H10ClNO | 详情 | 详情 |