Hydrochloric Acid → 2-(4-((2,4-Dioxothiazolidin-5-YL)methyl)phenoxy)acetic acid

Participants

Reaction Conditions

Reaction Steps

A suspension of 5-[4-[(carbomethoxy)methoxy]benzyl]thiazolidine-2,4-dione obtained by following a procedure described in any of Examples 23-24 (135 g, 0.46 M) and water (540 ml, 4 times w/v) was taken in a round bottom flask fitted with a mechanical stirrer. Aq. sodium hydroxide solution (37 g of NaOH in 135 ml of water) was added slowly over a period of 5-10 minutes at 20-25° C. Stirring was continued at ambient temperature for a period of 2-3 h, while monitoring the reaction by TLC. After the completion of the reaction, the pH of the reaction mixture was adjusted to 2 using conc. HCl (temp. raises to 40-45° C.) and allowed to attain room temperature. The mass was cooled to 10-15° C. and the solid thus obtained was filtered and dried at 60-70° C. under 1-2 mm Hg of vacuum to afford 5-[4-[(carboxy)methoxy]benzyl]thiazolidine-2,4-dione (121 g, Y=99%, P=99.2%).

Provenance & Evidence