tert-butyl 2-(2-hydroxyethoxy)ethylcarbamate -Drug Synthesis Database

【结构式】

【分子编号】57574

【品名】tert-butyl 2-(2-hydroxyethoxy)ethylcarbamate

【CA登记号】

【分子式】C₉H₁₉NO₄

【分子量】205.2542

【元素组成】C 52.67% H 9.33% N 6.82% O 31.18%

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：(VIII)

The Boc-protected amino alcohol (VIII) is condensed with ethyl bromoacetate (IX) in the presence of potassium tert-butoxide to afford ether (X). After alkaline hydrolysis of the ethyl ester group of (X), the resultant carboxylic acid (XI) is activated as the thioimide (XIII) upon treatment with thiazolidine-2-thione (XII) and EDC. Coupling of the acyl thiazolidinone (XIII) with cytosine arabinoside (XIV) leads to the N-acyl cytosine derivative (XV). The Boc protecting group of (XV) is then removed under acidic conditions to furnish amine (XVI).

参考文献中间体

合成目标

【1】 Choe, Y.H.; et al.; Anticancer drug delivery systems: multi-loaded N-4-acyl poly(ethylene glycol) prodrugs of ara-C. II. Efficacy in ascites and solid tumors. J Control Release 2002, 79, 1-3, 55.

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(VIII)	57574	tert-butyl 2-(2-hydroxyethoxy)ethylcarbamate		C₉H₁₉NO₄	详情	详情
(IX)	16640	Ethyl 2-bromoacetate; Ethyl bromoacetate	105-36-2	C₄H₇BrO₂	详情	详情
(X)	57575	ethyl 2,2-dimethyl-4-oxo-3,8,11-trioxa-5-azatridecan-13-oate		C₁₃H₂₅NO₆	详情	详情
(XI)	57576	2,2-dimethyl-4-oxo-3,8,11-trioxa-5-azatridecan-13-oic acid		C₁₁H₂₁NO₆	详情	详情
(XII)	54751	Thiazolidine-2-thione		C₃H₅NS₂	详情	详情
(XIII)	57577	tert-butyl 2-{2-[2-oxo-2-(2-thioxo-1,3-thiazolidin-3-yl)ethoxy]ethoxy}ethylcarbamate		C₁₄H₂₄N₂O₅S₂	详情	详情
(XIV)	32709	Cytarabine; Cytosine Beta-D-Arabinofuranoside; 4-amino-1-[(2R,3S,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydro-2-furanyl]-2(1H)-pyrimidinone	147-94-4	C₉H₁₃N₃O₅	详情	详情
(XV)	57578	tert-butyl 2-{2-[2-({1-[(2R,3S,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydro-2-furanyl]-2-oxo-1,2-dihydro-4-pyrimidinyl}amino)-2-oxoethoxy]ethoxy}ethylcarbamate		C₂₀H₃₂N₄O₁₀	详情	详情
(XVI)	57579	2-[2-(2-aminoethoxy)ethoxy]-N-{1-[(2R,3S,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydro-2-furanyl]-2-oxo-1,2-dihydro-4-pyrimidinyl}acetamide		C₁₅H₂₄N₄O₈	详情	详情

Extended Information