Novel side reactions accompanying activation and aminolysis of N-benzoyl-2-alkylserines.
2-Phenyl-4-alkyl-4-hydroxymethyl-1,3-oxazolones (2a-d) have been identified as side products accompanying activation of N-benzoyl-2-alkylserines (1a-d). Oxazolones 2a-d in the presence of amine rearrange subsequently to corresponding 4-alkyl-2-phenyl-4,5-dihydro-1,3-oxazole-5 carboxylic acids (4a-d) at a 20-68% yield.
Kamiński
Z J
ZJ
Institute of Organic Chemistry, Technical University of Lódź, Poland. kaminsz@ck-sg.p.lodz.pl
Woszczyna
A
A
Kolesińska
B
B
Redliński
A
A
D000596:Amino Acids / Q000737:chemistry; D002264:Carboxylic Acids / Q000737:chemistry; D008956:Models, Chemical; D010081:Oxazolone / Q000737:chemistry*; D012694:Serine / Q000737:chemistry*; D013237:Stereoisomerism
D000596:Amino Acids; D002264:Carboxylic Acids; D010081:Oxazolone; D012694:Serine