2-ethoxyacetic acid -Drug Synthesis Database

【结构式】

【分子编号】24966

【品名】2-ethoxyacetic acid

【CA登记号】627-03-2

【分子式】C₄H₈O₃

【分子量】104.10572

【元素组成】C 46.15% H 7.75% O 46.11%

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：(II)

The cyclization of the diaminoquinoline (I) with ethoxyacetic acid (II) by heating at 120 C gives the imidazoquinoline (III), which is oxidized to the 5-N-oxide (IV) by treatment with peracetic acid. Finally, compound (IV) is aminated by means of ammonium hydroxide and p-toluenesulfonyl chloride in dichloromethane.

参考文献中间体

合成目标

【1】 Graul, A.; Castañer, J.; S-28463. Drugs Fut 1999, 24, 6, 622.
【2】 Nikolaides, N.; Lindstrom, K.J. (3M Pharmaceuticals); Process for preparing quinolone amines. WO 9417043 .

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)	24965	1-[(3-amino-4-quinolinyl)amino]-2-methyl-2-propanol		C₁₃H₁₇N₃O	详情	详情
(II)	24966	2-ethoxyacetic acid	627-03-2	C₄H₈O₃	详情	详情
(III)	24967	1-[2-(ethoxymethyl)-1H-imidazo[4,5-c]quinolin-1-yl]-2-methyl-2-propanol		C₁₇H₂₁N₃O₂	详情	详情
(IV)	24968	2-(ethoxymethyl)-1-(2-hydroxy-2-methylpropyl)-1H-imidazo[4,5-c]quinolin-5-ium-5-olate		C₁₇H₂₁N₃O₃	详情	详情

合成路线2

该中间体在本合成路线中的序号：(XXI)

Coupling of taxane intermediate (XIII) with benzyloxyacetic acid (XXI) in the presence of DCC and DMAP provided ester (XXII). After hydrogenolytic deprotection of the benzyl group of (XXII), the resulting hydroxyacetate ester (XXIII) was further condensed with N-carbobenzoxy-L-aspartic acid 1-amide (XXIV) to yield (XXV). Deprotection of the trichloroethoxycarbonyl groups of (XXV) with Zn and AcOH gave (XXVI). Finally, hydrogenolytic cleavage of the N-carbobenzoxy group of (XXVI) in the presence of p-toluenesulfonic acid furnished the title compound.

参考文献中间体

合成目标

【1】 Tsujihari, K.; Hashiyama, T.; Ohashi, M.; Nakanishi, N. (Tanabe Seiyaku Co., Ltd.); Baccatin derivs. and processes for preparing the same. CA 2162759; EP 0712854; JP 1997151181; US 5589502 .

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(XIII)	26472	methyl (9S,12S)-4-methoxy-12-[[(2S,5S,8S,11R)-5-(4-methoxybenzyl)-2,6,8,11,15,15-hexamethyl-4,7,10,13-tetraoxo-14-oxa-3,6,9,12-tetraazahexadec-1-anoyl](methyl)amino]-11-oxo-2-oxa-10-azatricyclo[12.2.2.1(3,7)]nonadeca-1(16),3(19),4,6,14,17-hexaene-9-carboxylate		C₄₉H₅₉Cl₆NO₁₈	详情	详情
(XXI)	24966	2-ethoxyacetic acid	627-03-2	C₄H₈O₃	详情	详情
(XXII)	26480	(1S,2S,3R,4S,7R,9S,10S,12R,15S)-4-(acetoxy)-15-([(2R,3S)-2-[[2-(benzyloxy)acetyl]oxy]-3-[(tert-butoxycarbonyl)amino]-3-cyclopropylpropanoyl]oxy)-1-hydroxy-10,14,17,17-tetramethyl-11-oxo-9,12-bis[[(2,2,2-trichloroethoxy)carbonyl]oxy]-6-oxatetracyclo[11.3.1.0(3,10).0(4,7)]heptadec-13-en-2-yl benzoate		C₅₅H₆₃Cl₆NO₂₀	详情	详情
(XXIII)	26481	(1S,2S,3R,4S,7R,9S,10S,12R,15S)-4-(acetoxy)-15-[[(2R,3S)-3-[(tert-butoxycarbonyl)amino]-3-cyclopropyl-2-(glycoloyloxy)propanoyl]oxy]-1-hydroxy-10,14,17,17-tetramethyl-11-oxo-9,12-bis[[(2,2,2-trichloroethoxy)carbonyl]oxy]-6-oxatetracyclo[11.3.1.0(3,10).0(4,7)]heptadec-13-en-2-yl benzoate		C₄₈H₅₇Cl₆NO₂₀	详情	详情
(XXIV)	26482	(3S)-4-amino-3-[[(benzyloxy)carbonyl]amino]-4-oxobutyric acid		C₁₂H₁₄N₂O₅	详情	详情
(XXV)	26483	(1S,2S,3R,4S,7R,9S,10S,12R,15S)-4-(acetoxy)-2-(benzoyloxy)-1-hydroxy-10,14,17,17-tetramethyl-11-oxo-9,12-bis[[(2,2,2-trichloroethoxy)carbonyl]oxy]-6-oxatetracyclo[11.3.1.0(3,10).0(4,7)]heptadec-13-en-15-yl (5S,12R)-5-(aminocarbonyl)-12-[(S)-[(tert-butoxycarbonyl)amino](cyclopropyl)methyl]-3,7,10-trioxo-1-phenyl-2,8,11-trioxa-4-azatridecan-13-oate		C₆₀H₆₉Cl₆N₃O₂₄	详情	详情
(XXVI)	26484	(1S,2S,3R,4S,7R,9S,10S,12R,15S)-4-(acetoxy)-2-(benzoyloxy)-1,9,12-trihydroxy-10,14,17,17-tetramethyl-11-oxo-6-oxatetracyclo[11.3.1.0(3,10).0(4,7)]heptadec-13-en-15-yl (5S,12R)-5-(aminocarbonyl)-12-[(S)-[(tert-butoxycarbonyl)amino](cyclopropyl)methyl]-3,7,10-trioxo-1-phenyl-2,8,11-trioxa-4-azatridecan-13-oate		C₅₄H₆₇N₃O₂₀	详情	详情

Extended Information