Rapid procedure for the hydrolysis of amides to acids

Abstract

Table I Asymmetric Synthesis of (lZ)-7-Butyrolactones 5 and (jR)-l,4-Butanediols 7 CD' [8,218 nm Compel R Yield, % " ta]23S89 (cEtOH) Optical purity, % (CH3CN)

Anionic synthesis of aromatic amide and carboxyl functionalized polymers. Chain-end functionalization of poly(styryl)lithium withN,N-diisopropyl-4-(1-phenylethenyl)benzamide

“…[33][34][35] However, attempts to effect the deprotection of the N,N-diisopropylamide group by the base-catalyzed hydrolysis of v-amidopolystyrene (2) with a potassium tert-butoxide and water slurry 41 in THF under reflux for 7 days produced only starting material as evidenced by FTIR analysis. Similarly, v-amidopolystyrene (2) was resistant to acid-catalyzed hydrolysis with 10% aqueous perchloric acid in THF.…”

A mild alkaline hydrolysis of N- and N,N-substituted amides and nitriles

“…The hydrolysis of amides and nitriles is a well studied reaction and numerous methods have been developed. [4][5][6][7][8][9][10][11][12][13][14] Among them, the use of sodium peroxide 4 and of phthalic anhydride 5 for the amide hydrolysis have been described, while nitriles can also be converted to amides by catalyzed hydration, [6][7][8][9] enzymatically 10 and on unactivated alumina. 11 Ames and Islip in their temperature, while primary and secondary amides were extremely resistant under the same conditions.…”

Synthesis of Potentially β-Blocking Practolol Derivatives: (E +Z)-3-[4-(3-Iodoprop-2-enyloxycarbonylamino)phenoxy]-1-(isopropylamino)propan-2-ol

“…However, although the latter is obtained very easily from practolol [7][8][9] or 4-aminophenol, it has the disadvantage of having two amine functions. We therefore had to first find a way of protecting only the secondary amine function.…”

“…Na 2 O 2 could also be used to hydrolyze the amide. [9] A mixture of 1 (3 g, 11.3 mmol) and Na 2 O 2 (1.76 g, 31.41 mmol) in water (110 mL) was heated at reflux and the reaction monitored by 1 H NMR (disappearance of the methyl singlet at δ ϭ 2.14). After 3 h, the mixture was extracted with CHCl 3 .…”