Facile ring opening reaction of oxazolone enables efficient amidation for aminoisobutyric acid
Abstract: 4,4-Dimethyloxazolones derived from N-protected aminoisobutyric acid (AIB) are particularly known as poor electrophiles due to the steric hindrance around the carbonyl and not employed as useful intermediates for amidation whereas numerous examp
Jo, Minmi,Won, Sun-Woo,Lee, Dong Guk,Yun, Jungeon,Kim, Sunhong,Kwak, Young-Shin
p. 481 - 489
(2018/05/03)
PS-IIDQ: a supported coupling reagent for efficient and general amide bond formation
Polystyrene-IIDQ, a polymer-supported coupling reagent, was synthesized in three steps from Merrifield resin in 86% overall conversion. This reagent efficiently coupled carboxylic acids to amines in good yields and high purities, required no pre-activation step, and was tolerant of the order of reagent addition. PS-IIDQ was observed to be more efficient than polymer-supported carbodiimides (PS-EDC and PS-DCC) and gave higher yields than HATU for general amide bond formation, including the coupling of anilines and hindered substrates. When evaluated with five carboxylic acids and nine amines (including anilines and secondary amines) PS-IIDQ gave an average isolated yield of 73%.
Valeur, Eric,Bradley, Mark
p. 8855 - 8871
(2008/02/11)
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