Cefteram pivoxil, Ro-19-5248, T-2588, Tomiron

头孢特仑新戊酯Chemical Name: [6R-(6alpha,7beta)]-7-[2-(2-Amino-4-thiazolyl)-2(Z)-(methoxyimino)acetamido]-3-(5-methyl-2H-tetrazol-2-ylmethyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid (2,2-dimethyl-1-oxopropoxy)methyl ester; (6R,7R)-7-[2-(2-Amino-4-thiazolyl)-2(Z)-(methoxyimino)acetamido]-3-(5-methyl-2H-tetrazol-2-ylmethyl)-3-cephem-4-carboxylic acid pivaloyloxymethyl ester
CAS No. 82547-81-7, 82556-89-6 (monoHCl)
项目整合开发状态: Launched-1987
项目研究机构: Toyama (Originator), Showa Sangyo (Comarketer)
合成路线: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.

合成路线: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.