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6849443 
Journal Article 
MILD HYDROLYSIS OR ALCOHOLYSIS OF AMIDES - TI(IV) CATALYZED CONVERSION OF PRIMARY CARBOXAMIDES TO CARBOXYLIC-ACIDS OR ESTERS 
Fisher, LE; Fisher, LE; Caroon, JM; Caroon, JM; Stabler, SR; Stabler, SR; Lundberg, S; Lundberg, S; Zaidi, S; Zaidi, S; Sorensen, CM; Sorensen, CM; Sparacino, ML; Sparacino, ML; Muchowski, JM; Muchowski, JM 
1994 
Yes 
Canadian Journal of Chemistry
ISSN: 0008-4042
EISSN: 1480-3291 
72 
1 
142-145 
WOS:A1994NB68100025 
Reaction of primary amides (e.g., 1a or 6-13) or O-methylhydroxamates (1b and 1c) with a catalytic amount of TiCl4 and one equivalent of aqueous HCl converts these compounds in good yields to carboxylic esters (when an alcohol is used as solvent) or to carboxylic acids (when 9:1 dioxane:H2O is used as solvent). These conversions are chemoselective for primary amides: mono- and dialkyl amides are not affected by the reaction conditions. The hydrolysis conditions described do not compromise the stereochemical integrity of an adjacent chiral center. This is exemplified by the hydrolysis of naproxen amide (34) to naproxen (33) without detectable racemization as determined by chiral HPLC.< 
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