Cefprozil, BMY-28100-03-800(monohydrate), BMY-28100, Cefzil, Procef
头孢丙烯 头孢丙烯 Chemical Name: (6R,7R)-7-[(R)-2-Amino-2-(p-hydroxyphenyl)acetamido]-8-oxo-3-[(Z)-propenyl]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid; (6R,7R)-7-[(R)-2-Amino-2-(4-hydroxyphenyl)acetamido]-3-[(Z)-propenyl]-3-cephem-4-carboxylic acid
CAS No. 92665-29-7, 121123-17-9 (monohydrate)
项目整合开发状态: Launched-1992
项目研究机构: Bristol-Myers Squibb (Originator), Domp?(Marketer)
合成路线:The partial hydrolysis of 7-(phenylacetamido) cephalosporanic acid (I) followed by esterification with diphenyldyazomethane (II) gives benzhydryl 3-(hydroxymethyl)-7-(phenylacetamido)-3-cephem-4-carboxylate (III),which by reaction with PCl5 affords benzhydryl 7-amino-3-(chloromethyl)-3- cephem-4-carboxylate (IV).The condensation of (IV) with N-(tert-butoxycarbonyl)-2(R)-(4-hydroxyphenyl) glycine (V) by means of dicyclohexylcarbodiimide (DCC) yields benzhydryl 7-[(R)-2-(tert-butoxycarbonylamino)-2-(4-hydroxypheny) acetamido]-3-(chloro-methyl)-3-cephem-4-carboxylate (VI),which by reaction with NaI in acetone is converted to the corresponding iodomethyl derivative (VII).The reaction of (VII) with triphenylphosphine in ethyl acetate affords the phosphonium salt (VIII),which is submitted to a Wittig condensation with acetaldehyde to yield benzhydryl 7-[(R)-2-(tert-butoxycarbonylamino)-2-(4-hydroxyphenyl)acetamido]-3-(propenyl)-3-cephem-4-carboxylate (IX).Finally this compound is deprotected by a treatment with trifluoroacetic acid.
📌 参考资料/链接：
参考文献标题:Substd.vinyl cephalosporins
文献作者:Aburaki,S.; Okumura,J.; Naito,T.; Abe,Y.; Hoshi,H.(Bristol-Myers Squibb Co.)
参考来源:BE 0898778; CH 661731; DE 3402642; ES 8600310; GB 2135305; JP 1986171486; US 4520022
📄 详细内容
合成路线:The partial hydrolysis of 7-(phenylacetamido) cephalosporanic acid (I) followed by esterification with diphenyldyazomethane (II) gives benzhydryl 3-(hydroxymethyl)-7-(phenylacetamido)-3-cephem-4-carboxylate (III),which by reaction with PCl5 affords benzhydryl 7-amino-3-(chloromethyl)-3- cephem-4-carboxylate (IV).The condensation of (IV) with N-(tert-butoxycarbonyl)-2(R)-(4-hydroxyphenyl) glycine (V) by means of dicyclohexylcarbodiimide (DCC) yields benzhydryl 7-[(R)-2-(tert-butoxycarbonylamino)-2-(4-hydroxypheny) acetamido]-3-(chloro-methyl)-3-cephem-4-carboxylate (VI),which by reaction with NaI in acetone is converted to the corresponding iodomethyl derivative (VII).The reaction of (VII) with triphenylphosphine in ethyl acetate affords the phosphonium salt (VIII),which is submitted to a Wittig condensation with acetaldehyde to yield benzhydryl 7-[(R)-2-(tert-butoxycarbonylamino)-2-(4-hydroxyphenyl)acetamido]-3-(propenyl)-3-cephem-4-carboxylate (IX).Finally this compound is deprotected by a treatment with trifluoroacetic acid.
参考文献标题:CEFPROZIL
文献作者:Serradell,M.N.; Castar,J.; Castar,R.M.
参考来源:Drugs Fut 1989,14(6),507
合成路线:The partial hydrolysis of 7-(phenylacetamido) cephalosporanic acid (I) followed by esterification with diphenyldyazomethane (II) gives benzhydryl 3-(hydroxymethyl)-7-(phenylacetamido)-3-cephem-4-carboxylate (III),which by reaction with PCl5 affords benzhydryl 7-amino-3-(chloromethyl)-3- cephem-4-carboxylate (IV).The condensation of (IV) with N-(tert-butoxycarbonyl)-2(R)-(4-hydroxyphenyl) glycine (V) by means of dicyclohexylcarbodiimide (DCC) yields benzhydryl 7-[(R)-2-(tert-butoxycarbonylamino)-2-(4-hydroxypheny) acetamido]-3-(chloro-methyl)-3-cephem-4-carboxylate (VI),which by reaction with NaI in acetone is converted to the corresponding iodomethyl derivative (VII).The reaction of (VII) with triphenylphosphine in ethyl acetate affords the phosphonium salt (VIII),which is submitted to a Wittig condensation with acetaldehyde to yield benzhydryl 7-[(R)-2-(tert-butoxycarbonylamino)-2-(4-hydroxyphenyl)acetamido]-3-(propenyl)-3-cephem-4-carboxylate (IX).Finally this compound is deprotected by a treatment with trifluoroacetic acid.
参考文献标题:Synthesis and structure-activity relationsships of a new oral cephalosporin,BMY-28100 and related compounds
文献作者:Winocour,P.; Vezina,M.; Kornbrust,D.; Sullivan,T.; Durkin,J.
参考来源:J Antibiot 1987,40(7),991
产品链接: CAS No. 92665-29-7›› 产品链接: CAS No.121123-17-9››