ethyl benzenecarboximidoate -Drug Synthesis Database

【结构式】

【分子编号】14225

【品名】ethyl benzenecarboximidoate

【CA登记号】

【分子式】C₉H₁₁NO

【分子量】149.19248

【元素组成】C 72.46% H 7.43% N 9.39% O 10.72%

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：(III)

D-Cycloserine can be obtained by several different ways: 1) The esterification of DL-serine (I) with methanol gives the methyl ester (II), which is cyclized with ethyl imidobenzoate (III) yielding 2-phenyl-2-oxazoline-4-carboxylic acid methyl ester (IV). The reaction of (IV) with hydroxylamine and sodium ethoxide affords the hydroxamic acid (V), which is treated with HCl in dioxane to give 2-benzamido-3-chloropropionohydroxamic acid (VI). The cyclization of (VI) with base, followed by acidification yields 4-benzamidoisoxazolidin-3-one (VII), which by treatment with methanolic HCl is converted to 3-(aminooxy)-DL-alanine methyl ester (VIII). The cyclization of (VIII) with KOH affords DL-4-aminoisoxazolidin-3-one as a racemic mixture, which is resolved with D-tartaric acid.

参考文献中间体

合成目标

【1】 Folkers, K.; Stammer, C.H.; Holly, F.W.; Wilson, A.N.; Synthesis of D-4-amino-3-isoxazolidone. J Am Chem Soc 1955, 77, 2, 2346-7.
【2】 Schlapfer, R.; Majnoni, S.; Furst, A.; Von Plattner, P.A.; Frick, H.; Boller, A.; Kirchensteiner, H.; Hegedus, B.; Spiegelberg, H.; Synthesis of 4-amino-3-isoxazolidinone (cycloserine) and some analogs. Helv Chim Acta 1957, 40, 5, 1531-52.
【3】 Prous, J.; Mealy, N.; Castaner, J.; D-Cycloserine. Drugs Fut 1994, 19, 11, 988.

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)	14223	DL-2-Amino-3-hydroxypropionic acid; DL-Serine; (+/-)-2-Amino-3-hydroxypropionic acid; Serine	302-84-1	C₃H₇NO₃	详情	详情
(II)	14224	Serine, methyl ester; methyl 2-amino-3-hydroxypropanoate	2104-89-4	C₄H₉NO₃	详情	详情
(III)	14225	ethyl benzenecarboximidoate		C₉H₁₁NO	详情	详情
(IV)	14226	methyl 2-phenyl-4,5-dihydro-1,3-oxazole-4-carboxylate		C₁₁H₁₁NO₃	详情	详情
(V)	14227	N-Hydroxy-2-phenyl-4,5-dihydro-1,3-oxazole-4-carboxamide		C₁₀H₁₀N₂O₃	详情	详情
(VI)	14228	N-[1-(Chloromethyl)-2-(hydroxyamino)-2-oxoethyl]benzamide		C₁₀H₁₁ClN₂O₃	详情	详情
(VII)	14229	N-(3-Oxotetrahydro-4-isoxazolyl)benzamide		C₁₀H₁₀N₂O₃	详情	详情
(VIII)	14230	methyl 2-amino-3-(aminooxy)propanoate		C₄H₁₀N₂O₃	详情	详情
(IX)	63865	4-amino-3-isoxazolidinone		C₃H₆N₂O₂	详情	详情

合成路线2

该中间体在本合成路线中的序号：(V)

The condensation of 1-(4-methoxyphenyl)piperazine (I) with ethyl chloroacetate (II) gives the expected condensation product (III), which by treatment with hydrazine in converted into the corresponding hydrazide (IV). The cyclization of (IV) with benzimidate (V) by heating at 180 C affords the triazole (VI), which is finally condensed with 4-fluorobenzyl chloride (VII) by means of NaH in DMF.

参考文献中间体

合成目标

【1】 Chytiroglou-Lada, A.; Filippatos, E.C.; Papakonstantinou-Garoufalias, S.S.; Papadaki-Valiraki, A.E.; Todoulou, O.G.; Synthesis, antifungal activity and antibacterial evaluation of some 3-piperazinylmethyl-5-aryl-1H-1,2,4-triazoles. Arzneim-Forsch Drug Res 1998, 48, 10, 1019.

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)	16312	1-(4-Methoxyphenyl)piperazine; Methyl 4-piperazinophenyl ether	38212-30-5	C₁₁H₁₆N₂O	详情	详情
(II)	16601	ethyl chloroacetate; ethyl 2-chloroacetate	105-39-5	C₄H₇ClO₂	详情	详情
(III)	25573	ethyl 2-[4-(4-methoxyphenyl)-1-piperazinyl]acetate		C₁₅H₂₂N₂O₃	详情	详情
(IV)	25574	2-[4-(4-methoxyphenyl)-1-piperazinyl]acetohydrazide		C₁₃H₂₀N₄O₂	详情	详情
(V)	14225	ethyl benzenecarboximidoate		C₉H₁₁NO	详情	详情
(VI)	25575	1-(4-methoxyphenyl)-4-[(5-phenyl-1H-1,2,4-triazol-3-yl)methyl]piperazine; methyl 4-[4-[(5-phenyl-1H-1,2,4-triazol-3-yl)methyl]-1-piperazinyl]phenyl ether		C₂₀H₂₃N₅O	详情	详情
(VII)	12354	4-Fluorobenzyl chloride; 1-(Chloromethyl)-4-fluorobenzene	352-11-4	C₇H₆ClF	详情	详情

Extended Information