2-(3-amino-2-oxo-2,3,4,5-tetrahydro-1H-1-benzazepin-1-yl)acetic acid -Drug Synthesis Database

【结构式】

【分子编号】30516

【品名】2-(3-amino-2-oxo-2,3,4,5-tetrahydro-1H-1-benzazepin-1-yl)acetic acid

【CA登记号】

【分子式】C₁₂H₁₄N₂O₃

【分子量】234.25484

【元素组成】C 61.53% H 6.02% N 11.96% O 20.49%

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 reaction of 2,3,4,5-tetrahydro-1H-(1)benzazepin-2-one (I) with PCl5 in hot xylene gives 3,3-dichloro-2,3,4,5-tetrahydro-1H-(1)benzazepin-2-one (II), which is treated with sodium acetate and reduced with H2 over Pd/C in acetic acid yielding 3-chloro-2,3,4,5-tetrahydro-1H-(1)benzazepin-2-one (III). The reaction of (III) with sodium azide in DMSO affords 3-azido-2,3,4,5-tetrahydro-1H-(1)benzazepin-2-one (IV), which is condensed with benzyl bromoacetate (V) by means of NaH in DMF giving 3-azido-1-(benzyloxycarbonylmethyl)-2,3,4,5-tetrahydro-1H-(1)benzazepin-2-one (VI). The treatment of (VI) with Raney-Ni in ethanol-water yields 3-amino-1-(benzyloxycarbonylmethyl)-2,3,4,5-tetrahydro-1H-(1)benzazepin-2-one (VII), which is debenzylated by hydrogenation with H2 over Pd/C in ethanol affording 3-amino-1-(carboxymethyl)-2,3,4,5-tetrahydro-1H-(1)benzazepin-2-one (VIII). Finally, this compound is condensed with ethyl 3-benzylpyruvate (IX) by means of sodium cyanoborohydride in methanol acetic acid.

参考文献中间体

合成目标

【1】 Watthey, J.W.H. (Novartis AG); Benzazepin-2-ones, process for their preparation, pharmaceutical preparations containing these compounds and the compounds for therapeutical use. EP 0072352; GB 2103614; JP 8338260 .
【2】 Castaner, J.; Serradell, M.N.; CGS-14824 A. Drugs Fut 1984, 9, 5, 317.

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)	30511	1,3,4,5-tetrahydro-2H-1-benzazepin-2-one		C₁₀H₁₁NO	详情	详情
(II)	30512	3,3-dichloro-1,3,4,5-tetrahydro-2H-1-benzazepin-2-one		C₁₀H₉Cl₂NO	详情	详情
(III)	30513	3-chloro-1,3,4,5-tetrahydro-2H-1-benzazepin-2-one		C₁₀H₁₀ClNO	详情	详情
(IV)	20891	3-azido-1,3,4,5-tetrahydro-2H-1-benzazepin-2-one		C₁₀H₁₀N₄O	详情	详情
(V)	12869	benzyl 2-bromoacetate	5437-45-6	C₉H₉BrO₂	详情	详情
(VI)	30514	benzyl 2-(3-azido-2-oxo-2,3,4,5-tetrahydro-1H-1-benzazepin-1-yl)acetate		C₁₉H₁₈N₄O₃	详情	详情
(VII)	30515	benzyl 2-(3-amino-2-oxo-2,3,4,5-tetrahydro-1H-1-benzazepin-1-yl)acetate		C₁₉H₂₀N₂O₃	详情	详情
(VIII)	30516	2-(3-amino-2-oxo-2,3,4,5-tetrahydro-1H-1-benzazepin-1-yl)acetic acid		C₁₂H₁₄N₂O₃	详情	详情
(IX)	20896	Ethyl 2-oxo-4-phenylbutanoate; 2-Oxo-4-phenylbutyric acid ethyl ester	64920-29-2	C₁₂H₁₄O₃	详情	详情

Extended Information