Water → 3-Hydroxy-5-(2-oxopyrrolidin-1-yl)benzoic acid

Participants

Reaction Conditions

Reaction Steps

To a solution of 3-amino-5-(2-oxo-pyrrolidin-1-yl)-benzoic acid (D6) (280 mg, 1.25 mmol, 1 equiv) in a mixture of 2N aqueous HCl solution (2.5 ml) and MeOH (5 ml) at 0° C. was added NaN3 (190 mg, 2.75 mmol, 2.2 equiv) portionwise over 20 min. H2O (5 ml) was added and the resulting mixture was heated at 90° C. for 1 h then cooled to room temperature and diluted with AcOEt. The two layers were separated and the aqueous phase was extracted twice with AcOEt (20 ml). The combined organic layers were washed with brine (20 ml), dried over MgSO4 and concentrated in vacuo to give a crude product which was triturated with Et2O/MeOH to give 3-hydroxy-5-(2-oxo-pyrrolidin-1-yl)-benzoic acid (D36) (110 mg, 40%) as a light tan solid.

Provenance & Evidence