2-({5-{[2-(acetyloxy)ethyl]amino}-2-[(4-{[(2-amino-4-oxo-3,4-dihydro-6-pteridinyl)methyl]amino}benzoyl)amino]-5-oxopentanoyl}amino)ethyl acetate -Drug Synthesis Database

【结构式】

【分子编号】59034

【品名】2-({5-{[2-(acetyloxy)ethyl]amino}-2-[(4-{[(2-amino-4-oxo-3,4-dihydro-6-pteridinyl)methyl]amino}benzoyl)amino]-5-oxopentanoyl}amino)ethyl acetate

【CA登记号】

【分子式】C₂₇H₃₃N₉O₈

【分子量】611.61488

【元素组成】C 53.02% H 5.44% N 20.61% O 20.93%

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：(IV)

Esterification of ethanolamine hydrochloride (I) by means of acetyl chloride in HOAc yields 2-aminoethyl acetate (II). The carboxyl groups of folic acid (III) are protected by coupling with amino ester (II) in the presence of EDC, to produce diamide (IV). Subsequent condensation of (IV)with dimethylformamide diethylacetal (DMF-DEA) gives formamidine (V). The 4-carbonyl group of (V) is then protected as the phenethyl ether (VII) by treatment with 4-nitrophenethyl alcohol (VI) under Mitsunobu coupling conditions.

参考文献中间体

合成目标

【1】 Frank, A.; Karn, H.; Spanig, H. (Abbott GmbH & Co. KG); Production of 1-hydroxyalkyl-5-nitroimidazoles. DE 2359625; FR 2253019; GB 1481349 .
【2】 Frank, A.; Dockner, T.; Karn, H. (Abbott GmbH & Co. KG); Process for the preparation of 1-(2-hydroxyethyl)-2-methyl-5-nitroimidazole of high purity. EP 0150407 .

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)	10259	Ethanol amine;Ethanolamine;2-Aminoethanol; 2-Amino-1-ethanol；2-Aminoethyl alcohol	141-43-5	C₂H₇NO	详情	详情
(II)	59032	2-aminoethyl acetate		C₄H₉NO₂	详情	详情
(III)	59033	N-(4-{[(2-amino-4-oxo-3,4-dihydro-6-pteridinyl)methyl]amino}benzoyl)glutamic acid		C₁₉H₁₉N₇O₆	详情	详情
(IV)	59034	2-({5-{[2-(acetyloxy)ethyl]amino}-2-[(4-{[(2-amino-4-oxo-3,4-dihydro-6-pteridinyl)methyl]amino}benzoyl)amino]-5-oxopentanoyl}amino)ethyl acetate		C₂₇H₃₃N₉O₈	详情	详情
(V)	59035	2-({5-{[2-(acetyloxy)ethyl]amino}-2-[(4-{[(2-{[(E)-(dimethylamino)methylidene]amino}-4-oxo-3,4-dihydro-6-pteridinyl)methyl]amino}benzoyl)amino]-5-oxopentanoyl}amino)ethyl acetate		C₃₀H₃₈N₁₀O₈	详情	详情
(VI)	32472	2-(4-nitrophenyl)-1-ethanol	100-27-6	C₈H₉NO₃	详情	详情
(VII)	59036	2-{[5-{[2-(acetyloxy)ethyl]amino}-2-({4-[({2-{[(E)-(dimethylamino)methylidene]amino}-4-[(4-nitrophenethyl)oxy]-6-pteridinyl}methyl)amino]benzoyl}amino)-5-oxopentanoyl]amino}ethyl acetate		C₃₈H₄₅N₁₁O₁₀	详情	详情

Extended Information