Benazepril hydrochloride, TWT-8154, CGS-14824A, Cibacene, Briem, Cibacen, Lotensin

合成路线:The reaction of 2(R)-hydroxy-4-phenyl butyric acid ethyl ester (I) with trifluoromethanesulfonic anhydride in dichloromethane gives the corresponding triflate (II),which is then condensed with the amino benzazepinone (III) by means of NMM in the same solvent to provide the target benazepril.

参考文献标题:Process for the preparation of benazepril
文献作者:Kumar,Y.; De,S.; Thaper,R.K.; Kumar,D.S.M.(Ranbaxy Laboratories Ltd.)
参考来源:WO 0276375


合成路线: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.

参考文献标题:CGS-14824 A
文献作者:Castar,J.; Serradell,M.N.
参考来源:Drugs Fut 1984,9(5),317


合成路线:A new synthesis of CGS-14824A is given: The reaction of 3-bromo-1-phenylpropane (I) with KCN gives 4-phenylbutyronitrile (II),which is hydrolyzed to the corresponding butyric acid (III).The cyclization of (III) with polyphosphoric acid affords 1-tetralone (IV),which is brominated to 2-bromo-1-tetralone (V) and treated with hydroxylamine to give the oxime (VI).The Beckman rearrangement of (VI) yields 3-bromo-2,3,4,5-tetrahydro-1H-(1)benzazepin-2-one (VII),which is treated with sodium azide to afford the azide derivative (VIII).The N-alkylation of (VIII) with ethyl bromoacetate (IX) by means of KOH and tetrabutylammonium bromide in THF gives the N-alkylated azide (X),which is reduced by catalytic hydrogenation to the corresponding amine (XI).The hydrolysis of the ester group of (XI) with NaOH yields the free acetic acid derivative (XII),which is finally reductocondensed with ethyl 2-oxo-4-phenylbutyrate (XIII) by means of sodium cyanoborohydride.
参考文献标题:Synthesis of 14C-labeled 3-([1-ethoxycarbonyl-3-phenyl-(1S)-propyl]amino)-2,3,4,5-tetrahydro-2-oxo-1H-1-(3S)-benzazepine-1-acetic acid hydrochloride ([14C]CGS 14824A)
文献作者:Chaudhuri,N.K.; Patera,R.; Markus,B.; Sung,M.-S.
参考来源:J Label Compd Radiopharm 1987,24(10),1177-84


产品链接: CAS No. 86541-74-4››

产品链接: CAS No.86541-75-5››