(2S)-2-Amino-3-(2-oxo-1,2-dihydro-4-quinolinyl)propionic acid -Drug Synthesis Database

【结构式】

【分子编号】10299

【品名】(2S)-2-Amino-3-(2-oxo-1,2-dihydro-4-quinolinyl)propionic acid

【CA登记号】

【分子式】C₁₂H₁₂N₂O₃

【分子量】232.23896

【元素组成】C 62.06% H 5.21% N 12.06% O 20.67%

与该中间体有关的原料药合成路线共 2 条

合成路线1 合成路线2

合成路线1

该中间体在本合成路线中的序号：(VIIS)

2) The same reaction sequence of (I) and (IVr) yields intermediates (Vs), (VIs) and (VIIs), and finally (S)-OPC-12759.

参考文献中间体

合成目标

【1】 Morita, S.; Yamasaki, K.; Shimizu, T.; Uchida, M.; Otsubo, K.; Kanbe, T.; Synthesis and antiulcer activity of optical isomers of 2-(4-chlorobenzoy lamino)-3-[2(1H)-quinolinon-4-yl]propionic acid (rebamipide). Chem Pharm Bull 1991, 39, 11, 2906.

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(IVR)	10296	(R)-2,5-Dihydro-3,6-dimethoxy-2-isopropylpyrazine; (3R)-3-Isopropyl-5-methoxy-3,6-dihydro-2-pyrazinyl methyl ether; (2R)-2-Isopropyl-3,6-dimethoxy-2,5-dihydropyrazine	109838-85-9	C₉H₁₆N₂O₂	详情	详情
(VS)	10297	2-Chloro-4-[[(2S,5R)-5-isopropyl-3,6-dimethoxy-2,5-dihydro-2-pyrazinyl]methyl]quinoline; (3R,6S)-6-[(2-Chloro-4-quinolinyl)methyl]-3-isopropyl-5-methoxy-3,6-dihydro-2-pyrazinyl methyl ether		C₁₉H₂₂ClN₃O₂	详情	详情
(VIS)	10298	methyl (2S)-2-amino-3-(2-chloro-4-quinolinyl)propanoate		C₁₃H₁₃ClN₂O₂	详情	详情
(VIIS)	10299	(2S)-2-Amino-3-(2-oxo-1,2-dihydro-4-quinolinyl)propionic acid		C₁₂H₁₂N₂O₃	详情	详情
(II)	10289	4-(Bromomethyl)-2-chloroquinoline		C₁₀H₇BrClN	详情	详情
(III)	10290	2-Chloro-4-(chloromethyl)quinoline		C₁₀H₇Cl₂N	详情	详情
(VIII)	10295	p-Chlorobenzoyl chloride; 4-Chlorobenzoyl chloride	122-01-0	C₇H₄Cl₂O	详情	详情

合成路线2

该中间体在本合成路线中的序号：(VII-S)

3) The methylation of 3-(2-oxo-1,2-dihydroquinolin-4-yl)-(R,S)-alanine (IX) with SOCl2 and methanol yields the corresponding methyl ester (X), which is submitted to optical resolution with D-(-)-mandelic acid, affording adducts (XII) and (XIII). The hydrolytic treatment of (XII) and (XIII) with HCl and propylene oxide finally yields isomers (VIIr) and (VIIs), already obtained. Racemic OPC-12759 can also be resolved into its optical isomers by treatment with brucine and fractionated crystallization.

参考文献中间体

合成目标

【1】 Morita, S.; Yamasaki, K.; Shimizu, T.; Uchida, M.; Otsubo, K.; Kanbe, T.; Synthesis and antiulcer activity of optical isomers of 2-(4-chlorobenzoy lamino)-3-[2(1H)-quinolinon-4-yl]propionic acid (rebamipide). Chem Pharm Bull 1991, 39, 11, 2906.

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(VII-S)	10299	(2S)-2-Amino-3-(2-oxo-1,2-dihydro-4-quinolinyl)propionic acid		C₁₂H₁₂N₂O₃	详情	详情
(VIIR)	10306	(2R)-2-Amino-3-(2-oxo-1,2-dihydro-4-quinolinyl)propionic acid		C₁₂H₁₂N₂O₃	详情	详情
(IX)	10301	2-Amino-3-(2-oxo-1,2-dihydro-4-quinolinyl)propionic acid		C₁₂H₁₂N₂O₃	详情	详情
(X)	10302	methyl 2-amino-3-(2-chloro-4-quinolinyl)propanoate		C₁₃H₁₃ClN₂O₂	详情	详情
(XI)	10303	(2R)-2-Hydroxy-2-phenylethanoic acid; R-(-)-Mandelic acid	611-71-2	C₈H₈O₃	详情	详情
(XII)	10304	compound with hydroxy-phenyl-acetic acid; 2-Amino-3-(2-oxo-1,2-dihydro-quinolin-4-yl)-propionic acid methyl ester		C₁₃H₁₄N₂O₃.C₈H₈O₃	详情	详情
(XIII)	10305	2-Amino-3-(2-oxo-1,2-dihydro-quinolin-4-yl)-propionic acid methyl ester; compound with hydroxy-phenyl-acetic acid		C₁₃H₁₄N₂O₃.C₈H₈O₃	详情	详情

Extended Information