5-methyl-2H-1,2,3,4-tetraazole -Drug Synthesis Database

【结构式】

【分子编号】24726

【品名】5-methyl-2H-1,2,3,4-tetraazole

【CA登记号】4076-36-2

【分子式】C₂H₄N₄

【分子量】84.08072

【元素组成】C 28.57% H 4.8% N 66.63%

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：(II)

The condensation of 7-aminocephalosporanic acid (I) with 5-methyltetrazole (II) by means of BF3-ethyl ether in sulfolane gives 7-amino-3-(5-methyl-1,2,3,4-tetrazol-2-ylmethyl)-3-cephem-4-carboxylic acid (III), which is esterified with diphenyldiazomethane (IV) as usual to the ester (V). The condensation of (V) with 2-(tert-amyloxycarboxamidothiazol-4-yl)- 2-(methoxyimino)acetic acid (VI) by means of ethyl chlorocarbonate and N-methylmorpholine in CH2Cl2 affords the fully protected compound (VII), which is finally deprotected with trifluoroacetic acid.

参考文献中间体

合成目标

【1】 Hirakawa, T.; Imaizumi, H.; Inaba, T.; Konishi, Y.; Narita, H.; Sadaki, H.; Saikawa, I.; Tai, M.; Taki, H.; Watanabe, Y. (Toyama Chemical Co., Ltd.); Cephalosporins. AU 8549860; AU 8549863; DE 3137854; US 4489072 .
【2】 Serradell, M.N.; Castaner, J.; Cefteram. Drugs Fut 1986, 11, 9, 732.

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)	15672	7-Aminocephalosporanic acid; 3-[(acetoxy)methyl]-7-amino-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid; 7-ACA		C₁₀H₁₂N₂O₅S	详情	详情
(II)	24726	5-methyl-2H-1,2,3,4-tetraazole	4076-36-2	C₂H₄N₄	详情	详情
(III)	24727	7-amino-3-[(5-methyl-2H-1,2,3,4-tetraazol-2-yl)methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid		C₁₀H₁₂N₆O₃S	详情	详情
(IV)	24728	2-diazopropane		C₃H₆N₂	详情	详情
(V)	24729	benzyl 7-amino-3-[(5-methyl-2H-1,2,3,4-tetraazol-2-yl)methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate		C₁₇H₁₈N₆O₃S	详情	详情
(VI)	24730	2-[2-[(hexanoyloxy)amino]-1,3-thiazol-4-yl]-2-(methoxyimino)acetic acid		C₁₂H₁₇N₃O₅S	详情	详情
(VII)	24731	benzhydryl 7-[[2-[2-[(hexanoyloxy)amino]-1,3-thiazol-4-yl]-2-(methoxyimino)acetyl]amino]-3-[(5-methyl-2H-1,2,3,4-tetraazol-2-yl)methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate		C₃₅H₃₇N₉O₇S₂	详情	详情

合成路线2

该中间体在本合成路线中的序号：(II)

The condensation of 7-aminocephalosporanic acid (I) with 5-methyltetrazole (II) by means of BF3 ethyl ether in sulfolane gives 7-amino-3-(5-methyl-1,2,3,4-tetrazol-2-ylmethyl)-3-cephem-4-carboxylic acid (III), which is esterified with pivaloyloxymethyl iodide (IV) by means of triethylamine in DMF yielding the corresponding ester (V). Finally, this compound it condensed with 2-(2-aminothiazol-4-yl)-2-(methoxyimino)acetic acid (VI) by means of POCl3 and dimethylacetamide in CH2Cl2.

参考文献中间体

合成目标

【1】 Hirakawa, T.; Imaizumi, H.; Inaba, T.; Konishi, Y.; Narita, H.; Sadaki, H.; Saikawa, I.; Tai, M.; Taki, H.; Watanabe, Y. (Toyama Chemical Co., Ltd.); Cephalosporins. AU 8549860; AU 8549863; DE 3137854; US 4489072 .
【2】 Serradell, M.N.; Castaner, J.; Cefteram. Drugs Fut 1986, 11, 9, 732.

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)	15672	7-Aminocephalosporanic acid; 3-[(acetoxy)methyl]-7-amino-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid; 7-ACA		C₁₀H₁₂N₂O₅S	详情	详情
(II)	24726	5-methyl-2H-1,2,3,4-tetraazole	4076-36-2	C₂H₄N₄	详情	详情
(III)	24727	7-amino-3-[(5-methyl-2H-1,2,3,4-tetraazol-2-yl)methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid		C₁₀H₁₂N₆O₃S	详情	详情
(IV)	24735	tert-Butyl 2-iodoacetate		C₆H₁₁IO₂	详情	详情
(V)	24736	[(2,2-dimethylpropanoyl)oxy]methyl 7-amino-3-[(5-methyl-2H-1,2,3,4-tetraazol-2-yl)methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate		C₁₆H₂₂N₆O₅S	详情	详情
(VI)	24737	2-(2-amino-1,3-thiazol-4-yl)-2-(methoxyimino)acetic acid	65872-41-5	C₆H₇N₃O₃S	详情	详情

Extended Information