合成路线:The esterification of 4-phenoxy-3-nitro-5-sulfamoylbenzoic acid (I) with methanol and H2SO4 gives the corresponding methyl ester (II),which is reduced with H2 over Raney-Ni in methanol yielding methyl 4-phenoxy-3-amino-5-sulfamoylbenzoate (III).The condensation of (III) with succinic anhydride (B) or succinoyl chloride (A) by means of pyridine in refluxing dioxane affords methyl 4-phenoxy-3N-succinimido-5-sulfamoylbenzoate (IV),which is reduced with borontrifluoride ethearate and NaBH4 in diglyme giving methyl 4-phenoxy-3-(1-pyrrolidinyl)-5-sulfamoylbenzoate (V).Finally,this compound is hydrolyzed with NaOH in water.
参考文献标题:5-Sulfamoylbenzoic acid derivatives carrying a heterocyclic substituent
文献作者:Bormann,D.; et al.
参考来源:DE 2419970; FR 2324298; GB 1504505; US 4010273
合成路线:The esterification of 4-phenoxy-3-nitro-5-sulfamoylbenzoic acid (I) with methanol and H2SO4 gives the corresponding methyl ester (II),which is reduced with H2 over Raney-Ni in methanol yielding methyl 4-phenoxy-3-amino-5-sulfamoylbenzoate (III).The condensation of (III) with succinic anhydride (B) or succinoyl chloride (A) by means of pyridine in refluxing dioxane affords methyl 4-phenoxy-3N-succinimido-5-sulfamoylbenzoate (IV),which is reduced with borontrifluoride ethearate and NaBH4 in diglyme giving methyl 4-phenoxy-3-(1-pyrrolidinyl)-5-sulfamoylbenzoate (V).Finally,this compound is hydrolyzed with NaOH in water.
参考文献标题:Piretanide (Hoe 118) a new high ceiling salidiuretic
文献作者:Merkel,W.; et al.
参考来源:Eur J Med Chem 1976,11(5),399
产品链接: CAS No. 55837-27-9››