tert-butyl (3R)-1-cyclohexyl-4-oxo-2,3,4,5-tetrahydro-1H-1,5-benzodiazepin-3-ylcarbamate -Drug Synthesis Database

【结构式】

【分子编号】49768

【品名】tert-butyl (3R)-1-cyclohexyl-4-oxo-2,3,4,5-tetrahydro-1H-1,5-benzodiazepin-3-ylcarbamate

【CA登记号】

【分子式】C₂₀H₂₉N₃O₃

【分子量】359.46868

【元素组成】C 66.83% H 8.13% N 11.69% O 13.35%

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：(VIII)

The condensation of the mono-protected 2,3-diaminopropionic acid (I) with 2-fluoronitrobenzene (II) produced the nitro acid (III). After catalytic hydrogenation of the nitro group of (III), the resulting amino acid (IV) was cyclized to the benzodiazepinone (V) upon refluxing in toluene. Alkylation of (V) with cyclohexenyl bromide (VI) afforded the 5-cyclohexenyl benzodiazepinone (VII), which was further hydrogenated to the cyclohexyl derivative (VIII). Acid cleavage of the Boc protecting group of (VIII) furnished the aminobenzodiazepinone (IX).

参考文献中间体

合成目标

【1】 Murata, M.; Shinozaki, K.; Yoneta, T.; Miura, N.; Maeda, K. (Zeria Pharmaceutical Co., Ltd.); 1,5-Benzodiazepine derivs.. EP 0945445; US 6239131; WO 9825911 .

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)	49763	Boc-D-diaminopropionic acid		C₈H₁₆N₂O₄	详情	详情
(II)	13463	o-Fluoronitrobenzene; 1-fluoro-2-nitrobenzene	1493-27-2	C₆H₄FNO₂	详情	详情
(III)	49764	(2R)-2-[(tert-butoxycarbonyl)amino]-3-(2-nitroanilino)propionic acid		C₁₄H₁₉N₃O₆	详情	详情
(IV)	49765	(2R)-3-(2-aminoanilino)-2-[(tert-butoxycarbonyl)amino]propionic acid		C₁₄H₂₁N₃O₄	详情	详情
(V)	49766	tert-butyl (3R)-2-oxo-2,3,4,5-tetrahydro-1H-1,5-benzodiazepin-3-ylcarbamate		C₁₄H₁₉N₃O₃	详情	详情
(VI)	30800	3-bromo-1-cyclohexene	1521-51-3	C₆H₉Br	详情	详情
(VII)	49767	tert-butyl (3R)-1-(2-cyclohexen-1-yl)-4-oxo-2,3,4,5-tetrahydro-1H-1,5-benzodiazepin-3-ylcarbamate		C₂₀H₂₇N₃O₃	详情	详情
(VIII)	49768	tert-butyl (3R)-1-cyclohexyl-4-oxo-2,3,4,5-tetrahydro-1H-1,5-benzodiazepin-3-ylcarbamate		C₂₀H₂₉N₃O₃	详情	详情
(IX)	49769	(3R)-3-amino-5-cyclohexyl-1,3,4,5-tetrahydro-2H-1,5-benzodiazepin-2-one		C₁₅H₂₁N₃O	详情	详情

Extended Information