Cefditoren pivoxil, ME-1207, Spectracef, Meiact

合成路线:The reaction of 3-(chloromethyl)-7-(phenylacetamido)-3-cephem-4-carboxylic acid 4-methoxybenzyl ester (I) with triphenylphosphine and NaI in acetone gives the corresponding phosphonium salt (II),which is condensed with 4-methylthiazole-5-carboxaldehyde (III) by means of NaHCO3 in dichloromethane affording 3-[2(Z)-(4-methylthiazol-5-yl)vinyl]-7-(phenylacetamido)-3-cephem-4-carboxylic acid 4-methoxybenzyl ester (IV).The cleavage of the amido group of (IV) with PCl5 and pyridine yields the 7-amino compound (V),which is condensed with 2-(methoxyimino)-2-[2-(tritylamino)thiazol-4-yl]acetic acid (VI) by means of POCl3 in dichloromethane giving 3-[2(Z)-(4-methylthiazol-5-yl)vinyl]-7-[2(Z)-methoxyimino)-2-(2-tritylamino)thiazol-4-yl)acetamido]-3-cephem-4-carboxylic acid 4-methoxybenzyl ester (VII).The deprotection of (VII) with trifluoroacetic acid and anisole yields the free amino acid (VIII),which is finally esterified with iodomethyl pivalate (IX) in DMF.

参考文献标题:Synthesis and oral activity of ME1207,a new orally active cephalosporin
文献作者:Sakagami,K.; Tamura,A.; Yoshida,T.; Nishihata,K.; Fukatsu,S.; Atsumi,K.
参考来源:J Antibiot 1990,43(8),1047


合成路线:The reaction of 3-(chloromethyl)-7-(phenylacetamido)-3-cephem-4-carboxylic acid 4-methoxybenzyl ester (I) with triphenylphosphine and NaI in acetone gives the corresponding phosphonium salt (II),which is condensed with 4-methylthiazole-5-carboxaldehyde (III) by means of NaHCO3 in dichloromethane affording 3-[2(Z)-(4-methylthiazol-5-yl)vinyl]-7-(phenylacetamido)-3-cephem-4-carboxylic acid 4-methoxybenzyl ester (IV).The cleavage of the amido group of (IV) with PCl5 and pyridine yields the 7-amino compound (V),which is condensed with 2-(methoxyimino)-2-[2-(tritylamino)thiazol-4-yl]acetic acid (VI) by means of POCl3 in dichloromethane giving 3-[2(Z)-(4-methylthiazol-5-yl)vinyl]-7-[2(Z)-methoxyimino)-2-(2-tritylamino)thiazol-4-yl)acetamido]-3-cephem-4-carboxylic acid 4-methoxybenzyl ester (VII).The deprotection of (VII) with trifluoroacetic acid and anisole yields the free amino acid (VIII),which is finally esterified with iodomethyl pivalate (IX) in DMF.

参考文献标题:Cefditoren Pivoxil
文献作者:Castar,J.; Prous,J.
参考来源:Drugs Fut 1992,17(8),665


合成路线:The reaction of 3-(chloromethyl)-7-(phenylacetamido)-3-cephem-4-carboxylic acid 4-methoxybenzyl ester (I) with triphenylphosphine and NaI in acetone gives the corresponding phosphonium salt (II),which is condensed with 4-methylthiazole-5-carboxaldehyde (III) by means of NaHCO3 in dichloromethane affording 3-[2(Z)-(4-methylthiazol-5-yl)vinyl]-7-(phenylacetamido)-3-cephem-4-carboxylic acid 4-methoxybenzyl ester (IV).The cleavage of the amido group of (IV) with PCl5 and pyridine yields the 7-amino compound (V),which is condensed with 2-(methoxyimino)-2-[2-(tritylamino)thiazol-4-yl]acetic acid (VI) by means of POCl3 in dichloromethane giving 3-[2(Z)-(4-methylthiazol-5-yl)vinyl]-7-[2(Z)-methoxyimino)-2-(2-tritylamino)thiazol-4-yl)acetamido]-3-cephem-4-carboxylic acid 4-methoxybenzyl ester (VII).The deprotection of (VII) with trifluoroacetic acid and anisole yields the free amino acid (VIII),which is finally esterified with iodomethyl pivalate (IX) in DMF.
参考文献标题:Synthesis and oral activity of pivaloyloxymethyl 7-[(Z)-2-(2-aminothiazol-4-yl)-2-methoxyiminoacetamido]-3(Z)--(4-methylthiazol-5-yl)vinyl-3-cephem-4-carboxylate (ME1207) and its related compound
文献作者:Yamamoto,Y.; Yoshida,T.; Tamura,A.; Atsumi,K.; Fukatsu,S.; Sakagami,K.; Nishihata,K.
参考来源:Chem Pharm Bull 1992,39(9),2433


产品链接: CAS No. 117467-28-4››