4-oxo-L-proline → Cis-4-Hydroxy-L-Proline

Chemical synthesis of 4-ketoproline derivatives from inexpensive achiral starting materials will typically produce a racemic mixture of two enantiomers. It has been reported that hydrogenation of either D- or L-enantiomer of 4-ketoproline derivatives can produce the corresponding cis-4-hydroxyproline derivatives with high selectivity (Kuhn et al., Chem. Ber. 89:1423 (1956)), so an enzymatic resolution of a racemic mixture of D- and L-4-ketoproline derivatives would allow for the hydrogenation of the 4-keto-D-proline derivative to produce CHDP. Chemical or enzymatic racemization of the remaining 4-keto-L-proline derivative to a 50/50 mixture of D- and L-isomers could allow the undesired L-isomer to be recycled back into the resolution step. Alternatively, if the 4-keto-L-proline derivative could be reduced and hydrolyzed to THLP, the THLP is readily converted to CHDP by chemical isomerization.

1. customwill typically produce
2. additiona racemic mixture of two enantiomers

ORDレコード

ord-3fc64090c0c144b29fa1fab641e7d69f

出典データセット

uspto-grants-1999_07

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US05928933