4-nitrophenyl 1-piperazinecarboxylate -Drug Synthesis Database

【结构式】

【分子编号】26809

【品名】4-nitrophenyl 1-piperazinecarboxylate

【CA登记号】

【分子式】C₁₁H₁₃N₃O₄

【分子量】251.24204

【元素组成】C 52.59% H 5.22% N 16.72% O 25.47%

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：(II)

Mercaptoproline derivative (I) was condensed with protected piperazine (II) via activation with carbonyl diimidazole to afford amide (III). The 4-methoxybenzyl group of (III) was then removed with trifluoromethanesulfonic acid in the presence of anisole and trifluoroacetic acid, and the resulting mercaptan (IV) was condensed with carbapenem phosphate (VI), (prepared from ketone (V) and diphenylphosphorochloridate), to afford thioether (VII). N-Methylation was carried out using methyl fluorosulfonate to yield quaternary ammonium salt (VIII). Finally, the 4-nitrobenzyl ester and carbamate groups of (VIII) were eliminated by hydrogenation in the presence of Pd/C, and the target product was isolated by ion-exchange chromatography.

参考文献中间体

合成目标

【1】 Ishikawa, K.; Kojima, K.; Miyauchi, M.; Endo, R.; Yasuda H; Kawamoto I.; Synthesis and structure-activity relationships of 1beta-methylcarbapenems with quaternary ammonium side chains. J Antibiot 1998, 51, 8, 757.
【2】 Kawamoto, I.; Miyauchi, M.; Nakayama, E.; Endo, R.; Ohya, S.; Utsui, Y. (Sankyo Co., Ltd.); Carbapenem derivs. having antibiotic activity, their preparation and their use. EP 0443883; JP 1992211083; US 5310735 .

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)	26808	(2S,4S)-4-[(4-methoxybenzyl)sulfanyl]-1-methyl-2-pyrrolidinecarboxylic acid		C₁₄H₁₉NO₃S	详情	详情
(II)	26809	4-nitrophenyl 1-piperazinecarboxylate		C₁₁H₁₃N₃O₄	详情	详情
(III)	26810	4-nitrobenzyl 4-([(2S,4S)-4-[(4-methoxybenzyl)sulfanyl]-1-methylpyrrolidinyl]carbonyl)-1-piperazinecarboxylate		C₂₆H₃₂N₄O₆S	详情	详情
(IV)	26811	4-nitrobenzyl 4-[[(2S,4S)-1-methyl-4-sulfanylpyrrolidinyl]carbonyl]-1-piperazinecarboxylate		C₁₈H₂₄N₄O₅S	详情	详情
(V)	22575	4-nitrobenzyl (2R,5R,6S)-6-[(1R)-1-hydroxyethyl]-4-methyl-3,7-dioxo-1-azabicyclo[3.2.0]heptane-2-carboxylate		C₁₇H₁₈N₂O₇	详情	详情
(VI)	13224	4-nitrobenzyl (4R,5R,6S)-3-[(diphenoxyphosphoryl)oxy]-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate	90776-59-3	C₂₉H₂₇N₂O₁₀P	详情	详情
(VII)	26812	4-nitrobenzyl (4R,5S,6S)-6-[(1R)-1-hydroxyethyl]-4-methyl-3-([(3S,5S)-1-methyl-5-[(4-[[(4-nitrobenzyl)oxy]carbonyl]-1-piperazinyl)carbonyl]pyrrolidinyl]sulfanyl)-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate		C₃₅H₄₀N₆O₁₁S	详情	详情
(VIII)	26813	(1R,5S,6S)-6-(1(R)-Hydroxyethyl)-2-[1,1-dimethyl-5(S)-[4-(4-nitrobenzyloxycarbonyl)piperazin-1-ylcarbonyl]pyrrrolidinium-3(S)-ylsulfanyl]-1-methyl-1-carba-2-penem-3-carboxylic acid 4-nitrobenzyl ester fluorosulfonate; (1R,5S,6S)-6-(1(R)-Hydroxyethyl)-2-[1,1-dimethyl-5(S)-[4-(4-nitrobenzyloxycarbonyl)piperazin-1-ylcarbonyl]pyrrrolidinium-3(S)-ylsulfanyl]-1-methyl-1-carba-2-penem-3-carboxylic acid 4-nitrobenzyl ester fluorosulfonate		C₃₆H₄₃FN₆O₁₄S₂	详情	详情

Extended Information