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【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

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.

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.

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