iodomethyl 3-[(tert-butoxycarbonyl)amino]propanoate -Drug Synthesis Database

【结构式】

【分子编号】57759

【品名】iodomethyl 3-[(tert-butoxycarbonyl)amino]propanoate

【CA登记号】

【分子式】C₉H₁₆INO₄

【分子量】329.13485

【元素组成】C 32.84% H 4.9% I 38.56% N 4.26% O 19.44%

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：(III)

Treatment of N-Boc-beta-alanine (I) with bromochloromethane gives the chloromethyl ester (II), which is further converted to the iodomethyl analogue (III) under the Finkelstein halide exchange reaction conditions. Condensation of iodomethyl ester (III) with 6-mercaptopurine (IV) provides adduct (V). The N-Boc group of (V) is then removed employing trifluoroacetic acid to furnish the amine compound (VI). Finally, EDC-mediated coupling of amine (VI) with the polyethyleneglycol-bound aspartic acid (VII) affords the title mercaptopurine prodrug.

参考文献中间体

合成目标

【1】 Choe, Y.H.; et al.; PEG prodrugs of 6-mercaptopurine (6-MP) - I: Synthesis and in vitro studies. Proc Am Assoc Cancer Res 2002, 43.

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)	26616	N-(tert-butoxycarbonyl)-beta-alanine	3303-84-2	C₈H₁₅NO₄	详情	详情
(II)	57758	chloromethyl 3-[(tert-butoxycarbonyl)amino]propanoate		C₉H₁₆ClNO₄	详情	详情
(III)	57759	iodomethyl 3-[(tert-butoxycarbonyl)amino]propanoate		C₉H₁₆INO₄	详情	详情
(IV)	11711	9H-Purine-6-thiol; 9H-Purin-6-ylhydrosulfide; 6-Mercaptopurine	50-44-2	C₅H₄N₄S	详情	详情
(V)	57760	(9H-purin-6-ylsulfanyl)methyl 3-[(tert-butoxycarbonyl)amino]propanoate		C₁₄H₁₉N₅O₄S	详情	详情
(VI)	57761	(9H-purin-6-ylsulfanyl)methyl 3-aminopropanoate		C₉H₁₁N₅O₂S	详情	详情
(VII)	65174			C₉H₁₄NO₇	详情	详情

Extended Information