2-carboperoxybenzoic acid -Drug Synthesis Database

【结构式】

【分子编号】34077

【品名】2-carboperoxybenzoic acid

【CA登记号】

【分子式】C₈H₆O₅

【分子量】182.13264

【元素组成】C 52.76% H 3.32% O 43.92%

与该中间体有关的原料药合成路线共 2 条

合成路线1 合成路线2

合成路线1

该中间体在本合成路线中的序号：(A)

C-10213-Go has been synthesized from 1-methyl-2-mercaptoimidazole (I). When (I) is methylated with methyl iodide it gives the corresponding thiomethyl derivative (II). Nitration of (II) yields the nitro derivative (III). Oxidation of (III) with monoperphthalic acid gives the sulfone (IV). Condensation of (IV) with 1-methanesulfonyl-2-imidazolidinone (VI) in the presence of sodium hydride affords C-10213-Go.

参考文献中间体

合成目标

【1】 Arya, V.P.; Satranidazole. Drugs Fut 1983, 8, 9, 797.

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(B)	13467	Methanesulfonyl chloride;Mesyl chloride;Methylsulfonyl chloride;Methanesulfonic acid chloride;Methanesulfonyl chloride;Methanesulphonyl chloride	124-63-0	CH₃ClO₂S	详情	详情
(A)	34077	2-carboperoxybenzoic acid		C₈H₆O₅	详情	详情
(I)	18783	1-methyl-1H-imidazol-2-ylhydrosulfide; 1-methyl-1H-imidazole-2-thiol	60-56-0	C₄H₆N₂S	详情	详情
(II)	36225	1-methyl-2-(methylsulfanyl)-1H-imidazole; methyl 1-methyl-1H-imidazol-2-yl sulfide		C₅H₈N₂S	详情	详情
(III)	36226	methyl 1-methyl-5-nitro-1H-imidazol-2-yl sulfide; 1-methyl-2-(methylsulfanyl)-5-nitro-1H-imidazole		C₅H₇N₃O₂S	详情	详情
(IV)	36227	1-methyl-2-(methylsulfonyl)-5-nitro-1H-imidazole; methyl 1-methyl-5-nitro-1H-imidazol-2-yl sulfone		C₅H₇N₃O₄S	详情	详情
(V)	36228	2-imidazolidinone	120-93-4	C₃H₆N₂O	详情	详情
(VI)	36229	1-(methylsulfonyl)-2-imidazolidinone	41730-79-4	C₄H₈N₂O₃S	详情	详情

合成路线2

该中间体在本合成路线中的序号：(B)

The starting product being 21-acetoxy-11alpha,17alpha-dihydroxy-pregn-4-ene-3,20-dione (I). The first step is the ketalization of (I) giving the ethylenedioxy derivative (II), which is epoxidized with monoperphthalic acid (B) to the epoxide (III), then the epoxide ring is opened with HF giving the fluoro derivative (IV); its bromination in dioxane affords (V), which by reaction with methanesulfonyl chloride gives the mesyl ester (VI). This compound is acetylated with acetic anhydride to the triacetoxy derivative (VII), which by treatment first with sodium acetate and then with bromine gives the mono unsaturated dibromo compound (VIII). This product by treatment with lithium carbonate and lithium bromide is converted into the triene derivative (IX); this product by treatment with 1,3-dibromo-5,5-dimethylhydantoine (C) adds BrOH giving (X), which is epoxidized by treatment with potassium carbonate yielding (Xl). This epoxide ring is finally opened with HF.

参考文献中间体

合成目标

【1】 Riva, M.; Toscano, L.; 2-Bromo-6beta-fluoropregna-1,4-3,20-diones. BE 0826030; DE 2533377; ES 455934; FR 2261776; GB 1499822 .
【2】 Castaner, J.; de Angelis, L.; Halopredone diacetate. Drugs Fut 1976, 1, 11, 526.

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(A)	11295	Polyethylene glycol;1,2-Ethanediol;Monoethylene glycol; Ethylene glycol	107-21-1	C₂H₆O₂	详情	详情
(B)	34077	2-carboperoxybenzoic acid		C₈H₆O₅	详情	详情
(I)	34075	2-[(8S,10R,11R,14S,17R)-11,17-dihydroxy-10-methyl-3-oxo-2,3,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]-2-oxoethyl acetate		C₂₂H₃₀O₆	详情	详情
(II)	34076			C₂₅H₃₆O₇	详情	详情
(III)	34078	(5α,6α,11α)-21-(acetyloxy)-5,6-epoxy-11,17-dihydroxypregnane-3,20-dione cyclic 3-(1,2-ethanediyl acetal)	57781-08-5	C₂₅H₃₆O₈	详情	详情
(IV)	34079	2-[(5R,6R,8S,10R,11R,13S,14S,17R)-6-fluoro-5,11,17-trihydroxy-10,13-dimethyl-3-oxohexadecahydro-1H-cyclopenta[a]phenanthren-17-yl]-2-oxoethyl acetate	913-49-5	C₂₃H₃₃FO₇	详情	详情
(V)	34080	2-[(2R,5R,6R,8S,10R,11R,13S,14S,17R)-2-bromo-6-fluoro-5,11,17-trihydroxy-10,13-dimethyl-3-oxohexadecahydro-1H-cyclopenta[a]phenanthren-17-yl]-2-oxoethyl acetate	57781-10-9	C₂₃H₃₂BrFO₇	详情	详情
(VI)	34081	2-((2R,5R,6R,8S,10R,11R,13S,14S,17R)-2-bromo-6-fluoro-5,17-dihydroxy-10,13-dimethyl-11-[[methyl(dimethylene)-lambda(6)-sulfanyl]oxy]-3-oxohexadecahydro-1H-cyclopenta[a]phenanthren-17-yl)-2-oxoethyl acetate		C₂₆H₃₈BrFO₇S	详情	详情
(VII)	34082	(2R,5R,6R,8S,10R,11R,13S,14S,17R)-5-(acetoxy)-17-[2-(acetoxy)acetyl]-2-bromo-6-fluoro-10,13-dimethyl-11-[[methyl(dimethylene)-lambda(6)-sulfanyl]oxy]-3-oxohexadecahydro-1H-cyclopenta[a]phenanthren-17-yl acetate		C₃₀H₄₂BrFO₉S	详情	详情
(VIII)	34083	(6R,8S,10R,11R,13S,14S,17R)-17-[2-(acetoxy)acetyl]-2,2-dibromo-6-fluoro-10,13-dimethyl-11-[[methyl(dimethylene)-lambda(6)-sulfanyl]oxy]-3-oxo-2,3,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl acetate		C₂₈H₃₇Br₂FO₇S	详情	详情
(IX)	34084	(6R,8S,10R,13S,14S,17R)-17-[2-(acetoxy)acetyl]-2-bromo-6-fluoro-10,13-dimethyl-3-oxo-6,7,8,10,12,13,14,15,16,17-decahydro-3H-cyclopenta[a]phenanthren-17-yl acetate	57808-78-3	C₂₅H₂₈BrFO₆	详情	详情
(X)	34085	(6R,8S,9R,10S,11S,13S,14S,17R)-17-[2-(acetoxy)acetyl]-2,9-dibromo-6-fluoro-11-hydroxy-10,13-dimethyl-3-oxo-6,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-3H-cyclopenta[a]phenanthren-17-yl acetate	57781-13-2	C₂₅H₂₉Br₂FO₇	详情	详情
(XI)	34086	(4aS,4bS,5aS,6aS,7R,9aS,9bS,11R)-7-[2-(acetoxy)acetyl]-3-bromo-11-fluoro-4a,6a-dimethyl-2-oxo-2,4a,5a,6,6a,7,8,9,9a,9b,10,11-dodecahydrocyclopenta[7,8]phenanthro[4b,5-b]oxiren-7-yl acetate		C₂₅H₂₈BrFO₇	详情	详情
(C)	31277	1,3-dibromo-5,5-dimethyl-2,4-imidazolidinedione	77-48-5	C₅H₆Br₂N₂O₂	详情	详情

Extended Information