N,N-dimethyl-2-(2-sulfanyl-2-adamantyl)acetamide -Drug Synthesis Database

【结构式】

【分子编号】58358

【品名】N,N-dimethyl-2-(2-sulfanyl-2-adamantyl)acetamide

【CA登记号】

【分子式】C₁₄H₂₃NOS

【分子量】253.40876

【元素组成】C 66.36% H 9.15% N 5.53% O 6.31% S 12.65%

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：(VI)

Thionation of 2-adamantanone (I) by means of P4S10 gives thioketone (II). Subsequent addition of tert-butyl acetate to thioadamantanone (II) furnishes the beta-mercapto ester (III). After acidic cleavage of the tert-butyl ester of (III), the resultant mercapto acid (IV) is cyclized to the thiolactone (V) by using EDC. Subsequent lactone ring opening in (V) with dimethylamine gives rise to amide (VI). Finally, the thiol group of (VI) is nitrosated with tert-butyl nitrite to provide the desired nitrosothio compound.

参考文献中间体

合成目标

【1】 Lin, C.-E.; et al.; Design and synthesis of nitrosylated paclitaxel (NO-paclitaxel) and adamantanyl nitric oxide donor as antirestenosis agents. 223rd ACS Natl Meet (April 7 2002, Orlando) 2002, Abst MEDI 36.

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)	40404	2-adamantanone	700-58-3	C₁₀H₁₄O	详情	详情
(II)	58354	2-adamantanethione		C₁₀H₁₄S	详情	详情
(III)	58355	tert-butyl 2-(2-sulfanyl-2-adamantyl)acetate		C₁₆H₂₆O₂S	详情	详情
(IV)	58356	2-(2-sulfanyl-2-adamantyl)acetic acid		C₁₂H₁₈O₂S	详情	详情
(V)	58357			C₁₂H₁₆OS	详情	详情
(VI)	58358	N,N-dimethyl-2-(2-sulfanyl-2-adamantyl)acetamide		C₁₄H₂₃NOS	详情	详情

Extended Information