phenyl carbamate -Drug Synthesis Database

【结构式】

【分子编号】33820

【品名】phenyl carbamate

【CA登记号】622-46-8

【分子式】C₇H₇NO₂

【分子量】137.13812

【元素组成】C 61.31% H 5.14% N 10.21% O 23.33%

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：(VIII)

The reaction of 3-acetyl-4-[3-(tert-butylamino)-2-hydroxypropoxy)aniline (VII) with phenyl carbamate (VIII) in pyridine gives the N-[3-acetyl-4-[3-(tert-butylamino)-2-hydroxypropoxy]phenylcarbamic acid phenyl ester (IX), which is tretated with diethylamine (X) in ethanol/water. By reaction of N-[3-acetyl-4-(3-chloro-2-hydroxypropoxy)phenyl]-N',N'-diethylurea (XI) with tert-butylamine (VI).

参考文献中间体

合成目标

【1】 Stormann-Menninger-Lerchenthal, H.; Pittner, H.; Zolss, G. (CL Pharma); 4-Ureido-2-acyl phenoxypropanolamine. DE 2458624; US 4034009 .

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(VI)	17895	2-Amino-2-methylpropane; tert-butylamine; 2-methyl-2-propanamine	75-64-9	C₄H₁₁N	详情	详情
(VII)	33819	1-[5-amino-2-[3-(tert-butylamino)-2-hydroxypropoxy]phenyl]-1-ethanone		C₁₅H₂₄N₂O₃	详情	详情
(VIII)	33820	phenyl carbamate	622-46-8	C₇H₇NO₂	详情	详情
(IX)	33821	phenyl 3-acetyl-4-[3-(tert-butylamino)-2-hydroxypropoxy]phenylcarbamate		C₂₂H₂₈N₂O₅	详情	详情
(X)	24486	Diethylamine; N,N-Diethylamine	109-89-7	C₄H₁₁N	详情	详情
(XI)	33822	N'-[3-acetyl-4-(3-chloro-2-hydroxypropoxy)phenyl]-N,N-diethylurea		C₁₆H₂₃ClN₂O₄	详情	详情

合成路线2

该中间体在本合成路线中的序号：(IV)

The intermediate carbamate (V) has been obtained as follows. The reaction of 4-bromo-3-methoxynitrobenzene (I) with CuCN in NMP at 150 C gives 2-methoxy-4-nitrobenzonitrile (II), which is reduced with H2 over Pd/C in ethyl acetate to yield 4-amino-2-methoxybenzonitrile (III). Finally, this compound is condensed with phenyl carbamate (IV) by means of NaHCO3 in ethyl acetate to afford the desired carbamate intermediate (V).

参考文献中间体

合成目标

【1】 Saunders, J.; Bethiel, S.; Badia, M.; Stamos, D.; Trudeau, M. (Vertex Pharmaceuticals Inc.); Inhibitors of IMPDH enzyme. WO 0056331 .

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)	51316	2-Bromo-5-nitroanisole	77337-82-7	C₇H₆BrNO₃	详情	详情
(II)	61931	2-methoxy-4-nitrobenzonitrile		C₈H₆N₂O₃	详情	详情
(III)	61932	4-amino-2-methoxybenzonitrile		C₈H₈N₂O	详情	详情
(IV)	33820	phenyl carbamate	622-46-8	C₇H₇NO₂	详情	详情
(V)	61933	phenyl 4-cyano-3-methoxyphenylcarbamate		C₁₅H₁₂N₂O₃	详情	详情

Extended Information