5-(benzoylamino)-4-oxopentanoic acid -Drug Synthesis Database

【结构式】

【分子编号】59156

【品名】5-(benzoylamino)-4-oxopentanoic acid

【CA登记号】

【分子式】C₁₂H₁₃NO₄

【分子量】235.23956

【元素组成】C 61.27% H 5.57% N 5.95% O 27.21%

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：(XXV)

Benzoylation of furfurylamine (XXI) under Schotten-Baumann conditions provided amide (XXII). The dimethoxy dihydrofuran derivative (XXIII) was then obtained as different diastereomeric mixtures by either the electrolysis of N-benzoylfurfurylamine (XXII) in the presence of NH4Cl in MeOH or by the bromination of (XXII) in MeOH. Oxidative cleavage of (XXIII) using the Jones reagent led to 5-benzamido-4-oxo-2-pentenoic acid (XXIV), which was further hydrogenated to the pentanoic analogue (XXV). Alternatively, (XXV) was also obtained by first hydrogenation of (XXIII) to the tetrahydrofuran (XXVI), which was then subjected to Jones oxidation. Finally, acidic hydrolysis of delta-benzamido levulinic acid (XXV) provided the title compound.

参考文献中间体

合成目标

【1】 Raphael, R.A.; Marei, A.A.; The synthesis of amino-acids from furfurylamine. J Chem Soc 1958, 2624.

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(XXI)	51396	1-(2-Furyl)methylamine; 2-Aminomethylfuran; 2-Furfurylamine; Furfurylamine	617-89-0	C₅H₇NO	详情	详情
(XXII)	59153	N-Furan-2-ylmethylbenzamide		C₁₂H₁₁NO₂	详情	详情
(XXIII)	59154	N-(2,5-Dimethoxy-2,5-dihydrofuran-2-ylmethyl)benzamide		C₁₄H₁₇NO₄	详情	详情
(XXIV)	59155	(E)-5-(benzoylamino)-4-oxo-2-pentenoic acid		C₁₂H₁₁NO₄	详情	详情
(XXV)	59156	5-(benzoylamino)-4-oxopentanoic acid		C₁₂H₁₃NO₄	详情	详情
(XXVI)	59157	N-[(2,5-dimethoxytetrahydro-2-furanyl)methyl]benzamide		C₁₄H₁₉NO₄	详情	详情

合成路线2

该中间体在本合成路线中的序号：(XXXV)

Tetrahydrofurfurylamine (XLVII) was converted into the corresponding phthalimide (XLVIII) by reaction of phthalic anhydride (V) in boiling chloroform. Subsequent ruthenium-catalyzed oxidation of (XLVIII) produced keto acid (XI), along with a pentanolide by-product, which was removed by column chromatography. Finally, acid hydrolysis of (XI) led to the desired compound. A closely related strategy was based in the ruthenium oxidation of N-benzoyl tetrahydrofurfurylamine (LXX), prepared from amine (XLVII) and benzoyl chloride (XLIX), to afford 5-benzoylaminolevulinic acid (XXXV), which was then hydrolyzed in boiling 6 N HCl .

参考文献中间体

合成目标

【1】 Kawakami, H.; et al.; A new synthesis of 5-aminolevulinic acid. Agric Biol Chem 1991, 55, 6, 1687.
【2】 Matsumoto, K.; Kawakami, H.; Koseki, K.; Ebata, T.; Matsushita, H. (Japan Tobacco Inc.); Method of preparing an acid additional salt of delta-aminolevulinic acid. US 5284973 .

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(V)	11900	2-Benzofuran-1,3-dione;1,2-Benzenedicarboxylic Anhydride;1,2-BENZENE DICARBOXYLIC ACID ANHYDRIDE;1,2-BENZENEDICARBONIC ACID, ANHYDRIDE;1,3-DIOXOPHTHALAN;1,3-ISOBENZOFURANDIONE;o-phthalic anhydride; Phthalic anhydride	85-44-9	C₈H₄O₃	详情	详情
(XI)	59147	5-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)-4-oxopentanoic acid		C₁₃H₁₁NO₅	详情	详情
(XXXV)	59156	5-(benzoylamino)-4-oxopentanoic acid		C₁₂H₁₃NO₄	详情	详情
(LXVII)	27335	Tetrahydro-2-furanylmethanamine; Tetrahydrofurfurylamine	4795-29-3	C₅H₁₁NO	详情	详情
(LXVIII)	59191	2-(tetrahydro-2-furanylmethyl)-1H-isoindole-1,3(2H)-dione		C₁₃H₁₃NO₃	详情	详情
(LXIX)	10463	Benzoyl chloride	98-88-4	C₇H₅ClO	详情	详情
(LXX)	59192	N-(tetrahydro-2-furanylmethyl)benzamide		C₁₂H₁₅NO₂	详情	详情

Extended Information