A novel synthesis of γ-carboxy-L-glutamic acid from L-5-oxoproline esters (Amino acids ; 8)

Effenberger, FranzMüller, WolfgangKeller, RolandWild, WolfgangZiegler, Thomas2009-08-272016-03-312009-08-272016-03-311990312179057http://nbn-resolving.de/urn:nbn:de:bsz:93-opus-43702http://elib.uni-stuttgart.de/handle/11682/1140http://dx.doi.org/10.18419/opus-1123N-Alkyl-L-5-oxoproline esters L-5 react with phosgene to form primarily the α-chloro enamines 6, which then react further to give the 4-carboxylated compounds 7. Solvolysis of the latter with an alcohol furnishes the alkyl N-alkyl-4-(alkoxycarbonyl)-L-5-oxoprolina 2L,4DL-8 in good yields. The dibenzyl N-benzhydryl ester 2L , 4L - 8 c can be converted simply to γ-carboxyglutamic acid (L-Gla) by way of the N-Boc-protected dibenzyl ester 2L,4DL-10.eninfo:eu-repo/semantics/openAccessAminosäuren , Solvolyse540A novel synthesis of γ-carboxy-L-glutamic acid from L-5-oxoproline esters (Amino acids ; 8)article