N,N-dialkoxycarbonylamino acids from the sodium hydride-mediated reaction of alkyl chloroformates with mixed anhydrides of N-alkoxycarbonylamino acids.
Reaction of mixed anhydride R1OCO-NHCHR2-CO-O-COOR3 for R1 = benzyl and tert-butyl and R3 = methyl, ethyl, benzyl and allyl with sodium hydride and R3OCOCl followed by acid hydrolysis gives modest yields of R1OCO-N(R3OCO)CHR2-COOH. The products are contaminated by parent acid R1OCO-NHCHR2-COOH that is not readily removed. About 75% of the acylation originates from intramolecular transfer of the alkyl carbonate moiety; the remainder comes from acylation by the alkyl chloroformate.
Benoiton
N L
NL
Department of Biochemistry, University of Ottawa, Ontario, Canada.
Akyurekli
D
D
Chen
F M
FM
D000596:Amino Acids / Q000138:chemical synthesis* / Q000737:chemistry; D000812:Anhydrides / Q000737:chemistry*; D002219:Carbamates / Q000138:chemical synthesis* / Q000737:chemistry; D005561:Formates / Q000737:chemistry*; D012964:Sodium / Q000737:chemistry*
D000596:Amino Acids; D000812:Anhydrides; D002219:Carbamates; D005561:Formates; D012964:Sodium