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【结 构 式】

【分子编号】14228

【品名】N-[1-(Chloromethyl)-2-(hydroxyamino)-2-oxoethyl]benzamide

【CA登记号】

【 分 子 式 】C10H11ClN2O3

【 分 子 量 】242.66172

【元素组成】C 49.5% H 4.57% Cl 14.61% N 11.54% O 19.78%

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:(VI)

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.

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
Extended Information