Sodium Hydroxide → Tert-butyl (2-oxo-2,3-dihydrobenzimidazol-1-yl)acetate

Participants

Reaction Steps

A solution of 2-oxo-2,3-dihydro-benzoimidazole-1-carboxylic acid ethyl ester (3 g, 14.78 mmol) (N. Meanwell et al, J. Org. Chem, 1995, 60(6), 1565-82) in THF (100 ml) was treated with BTPP(5.4 ml, 17.74 mmol) followed by t-butylbromoacetate (2.4 ml, 16.3 mmol) and the mixture was stirred for 30 minutes. The solution was diluted with ether and washed with water, dired over MgSO4 and concentrated. The residue was dissolved in MeOH (30 ml) and treated with NaOH (10 N, 3 ml, 30 mmol) and stirred for 1 h at 23° C. The solvent was removed and the residue diluted with ether and washed with 1N HCl, saturated NaCl dried over MgSO4 and concentrated. The residue was purified by flash chromatography to give 1.84 g (50%) (2-oxo-2,3-dihydro-benzoimidazol-1-yl)-acetic acid tert-butyl ester as a white solid.

Provenance & Evidence