【结 构 式】 |
【分子编号】14229 【品名】N-(3-Oxotetrahydro-4-isoxazolyl)benzamide 【CA登记号】 |
【 分 子 式 】C10H10N2O3 【 分 子 量 】206.20108 【元素组成】C 58.25% H 4.89% N 13.59% O 23.28% |
合成路线1
该中间体在本合成路线中的序号:(VII)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 |