methyl (2S)-1-(2-nitrobenzoyl)-2-pyrrolidinecarboxylate -Drug Synthesis Database

【结构式】

【分子编号】36812

【品名】methyl (2S)-1-(2-nitrobenzoyl)-2-pyrrolidinecarboxylate

【CA登记号】

【分子式】C₁₃H₁₄N₂O₅

【分子量】278.26464

【元素组成】C 56.11% H 5.07% N 10.07% O 28.75%

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：(IV)

The reaction of 2-nitrobenzoic acid with SOCl2 gives the acyl chloride (II), which is condensed with D-proline (III) by means of TEA in dichloromethane yielding the acyl proline (IV). The reductive cyclization of (IV) with H2 over Pd/C in methanol affords the pyrrolobenzodiazepinedione (V). The selective reduction of the C-11 lactam group of (V) with NaBH4 and TFA in glyme gave the pyrrolobenzodiazepinone (VI), which is finally coupled with 4-[(2-phenylbenzoyl)amino]benzoyl chloride (VII) furnishing the title compound.

参考文献中间体

合成目标

【1】 Naito, A.; Ohtake, Y.; Hasegawa, H.; et al.; Novel vasopressin V2 receptor-selective antagonists, pyrrolo[2,1-a]quinoxaline and pyrrolo[2,1-c][1,4]benzodiazepine derivatives. Bioorg Med Chem 1999, 7, 6, 1247.
【2】 Matsukawa, H.; Toyofuku, H.; Naito, A.; Ohtake, Y.; Saito, Y.; Naito, K. (Wakamoto Pharmaceutical Co., Ltd.); Biphenyl derivs. and medicinal compsns.. EP 0987266; WO 9843976 .

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)	20951	2-nitrobenzoic acid；o-Nitrobenzoic acid	552-16-9	C₇H₅NO₄	详情	详情
(II)	21099	o-nitrobenzoyl chloride; 2-nitrobenzoyl chloride	610-14-0	C₇H₄ClNO₃	详情	详情
(III)	29552	methyl (2S)-2-pyrrolidinecarboxylate	2133-40-6	C₆H₁₁NO₂	详情	详情
(IV)	36812	methyl (2S)-1-(2-nitrobenzoyl)-2-pyrrolidinecarboxylate		C₁₃H₁₄N₂O₅	详情	详情
(V)	36813	(11aS)-2,3-dihydro-1H-pyrrolo[2,1-c][1,4]benzodiazepine-5,11(10H,11aH)-dione		C₁₂H₁₂N₂O₂	详情	详情
(VI)	36814	(11aS)-2,3,5,10,11,11a-hexahydro-1H-pyrrolo[2,1-c][1,4]benzodiazepine		C₁₂H₁₆N₂	详情	详情
(VII)	36810	4-[([1,1'-biphenyl]-2-ylcarbonyl)amino]benzoyl chloride		C₂₀H₁₄ClNO₂	详情	详情
(VIII)	29797	2H-3,1-benzoxazine-2,4(1H)-dione；Isatoic anhydride;4H-3,1-Benzoxazine-2,4(1H)-dione；1,2-Dihydro-4H-3,1-benzoxazine-2,4-dione;1H-benzo[d][1,3]oxazine-2,4-dione	118-48-9	C₈H₅NO₃	详情	详情

Extended Information