(4R)-N-(tert-butyl)-3-((2S,3S)-3-[[2-(2,6-dimethylphenoxy)acetyl]amino]-2-hydroxy-4-phenylbutanoyl)-5,5-dimethyl-1,3-thiazolidine-4-carboxamide -Drug Synthesis Database

【结构式】

【分子编号】45467

【品名】(4R)-N-(tert-butyl)-3-((2S,3S)-3-[[2-(2,6-dimethylphenoxy)acetyl]amino]-2-hydroxy-4-phenylbutanoyl)-5,5-dimethyl-1,3-thiazolidine-4-carboxamide

【CA登记号】

【分子式】C₃₀H₄₁N₃O₅S

【分子量】555.73876

【元素组成】C 64.84% H 7.44% N 7.56% O 14.39% S 5.77%

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)

Coupling of AZT (I) with Boc-Gly-OH (II) by means of dicyclohexyl carbodiimide (DCC) in the presence of dimethylaminopyridine (DMAP) in DMF followed by Boc removal by treatment with HCl/dioxane yields AZT ester (III). On the other hand, KNI-727 (IV) is condensed with glutaric anhydride (V) in THF-ether in the presence of dicyclohexylamine (DCHA) to yield the half ester of KNI-727 (VI), which is then condensed with derivative (III) by means of EDC.HCl in DMF in the presence of HOBt to furnish the target compound.

参考文献中间体

合成目标

【1】 Sano, K.; Kimura, T.; Hamawaki, T.; Matsumoto, H.; Ota, H.; Hayashi, Y.; Kiso, Y.; Goto, T.; "Double-drugs" - a new class of prodrug form of an HIV protease inhibitor conjugated with a reverse transcriptase inhibitor by a spontaneously cleavable linker. Bioorg Med Chem Lett 2000, 10, 11, 1227.

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)	45465	1-[(4S,5S)-4-azido-5-(hydroxymethyl)isoxazolidinyl]-5-methyl-2,4(1H,3H)-pyrimidinedione		C₉H₁₂N₆O₄	详情	详情
(II)	18066	N-alpha-t-BOC-glycine; 2-[(tert-butoxycarbonyl)amino]acetic acid	4530-20-5	C₇H₁₃NO₄	详情	详情
(III)	45466	[(4S,5S)-4-azido-2-[5-methyl-2,4-dioxo-3,4-dihydro-1(2H)-pyrimidinyl]isoxazolidinyl]methyl 2-aminoacetate		C₁₁H₁₅N₇O₅	详情	详情
(IV)	45467	(4R)-N-(tert-butyl)-3-((2S,3S)-3-[[2-(2,6-dimethylphenoxy)acetyl]amino]-2-hydroxy-4-phenylbutanoyl)-5,5-dimethyl-1,3-thiazolidine-4-carboxamide		C₃₀H₄₁N₃O₅S	详情	详情
(V)	15512	Glutaric Anhydride; dihydro-2H-pyran-2,6(3H)-dione	108-55-4	C₅H₆O₃	详情	详情
(VI)	45468	5-[((1S,2S)-1-([(4R)-4-[(tert-butylamino)carbonyl]-5,5-dimethyl-1,3-thiazolidin-3-yl]carbonyl)-2-[[2-(2,6-dimethylphenoxy)acetyl]amino]-3-phenylpropyl)oxy]-5-oxopentanoic acid		C₃₅H₄₇N₃O₈S	详情	详情

Extended Information