Reaction #969887

ord-7d7a30e5301d4af198e645938ca0c996

Reaction equation

Cc1ccc(S(=O)(=O)O)cc1
p-toluenesulphonic acid
CCc1ccc(CCOc2ccc(C[C@H]3SC(=O)NC3=O)cc2)nc1.O=C(O[C@@H](C(=O)O)[C@@H](OC(=O)c1ccccc1)C(=O)O)c1ccccc1
(5R)-5-{4-[2-(5-ethylpyridin-2-yl)ethoxy]benzyl}-1,3-thiazolidine-2,4-dione (−)-O,O′-dibenzoyl-L-tartrate
→
CCc1ccc(CCOc2ccc(C[C@H]3SC(=O)NC3=O)cc2)nc1.Cc1ccc(S(=O)(=O)O)cc1
(5R)-5-{4-[2-(5-ethylpyridin-2-yl)ethoxy]benzyl}-1,3-thiazolidine-2,4-dione tosylate

Reactants

Cc1ccc(S(=O)(=O)O)cc1
p-toluenesulphonic acid
CCc1ccc(CCOc2ccc(C[C@H]3SC(=O)NC3=O)cc2)nc1.O=C(O[C@@H](C(=O)O)[C@@H](OC(=O)c1ccccc1)C(=O)O)c1ccccc1
(5R)-5-{4-[2-(5-ethylpyridin-2-yl)ethoxy]benzyl}-1,3-thiazolidine-2,4-dione (−)-O,O′-dibenzoyl-L-tartrate

Reagents

None

Solvents

CC(C)O
IPA

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Procedure

To a solution of p-toluenesulphonic acid (0.8 g) in IPA (12 mL) at 40° C. was added (5R)-5-{4-[2-(5-ethylpyridin-2-yl)ethoxy]benzyl}-1,3-thiazolidine-2,4-dione (−)-O,O′-dibenzoyl-L-tartrate

Source

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