Reaction #969889

ord-a1d64ffa47914ff0add7c2fa22c7cfca

Reaction equation

CCc1ccc(CCOc2ccc(/C=C3/SC(=O)NC3=O)cc2)nc1
5-[1-{4-[2-(5-ethyl-pyridin-2-yl)-ethoxy]-phenyl}-meth-(E)-ylidene]-thiazolidine-2,4-dione
CN(CCOc1ccc(CC2SC(=O)NC2=O)cc1)c1ccccn1
Rosiglitazone
→
CCc1ccc(CCOc2ccc(C[C@H]3SC(=O)NC3=O)cc2)nc1
(R)-5-{4-[2-(5-ethyl-pyridin-2-yl)-ethoxy]-benzyl}-thiazolidine-2,4-dione

Reactants

CCc1ccc(CCOc2ccc(/C=C3/SC(=O)NC3=O)cc2)nc1
5-[1-{4-[2-(5-ethyl-pyridin-2-yl)-ethoxy]-phenyl}-meth-(E)-ylidene]-thiazolidine-2,4-dione
CN(CCOc1ccc(CC2SC(=O)NC2=O)cc1)c1ccccn1
Rosiglitazone

Reagents

None

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Procedure

Biocatalytic reduction of 5-[1-{4-[2-(5-ethyl-pyridin-2-yl)-ethoxy]-phenyl}-meth-(E)-ylidene]-thiazolidine-2,4-dione was investigated using literature procedures described for Rosiglitazone (J. Chem. Soc. Perkin Trans. I, 1994, 3319-3324).

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US08236786B2uspto-grants-2012_08