Ammonium Bicarbonate → 2-((1R)-1-(tert-butoxycarbonylamino)-2-(2-naphthyl)ethyl)-5-phenyl-1,3-thiazole-4-carboxylic acid amide

Participants

Reaction Steps

2-((1R)-1-(tert-Butoxycarbonylamino)-2-(2-naphthyl)ethyl)-5-phenyl-1,3-thiazole-4-carboxylic acid (0.17 g; 0.362 mmol) was dissolved in methylene chloride (8 ml). 1-Hydroxybenzotriazole (0.049 g; 0.362 mmol) and N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (0.083 g; 0.434 mmol) were added. The reaction mixture was stirred 15 min at room temperature. Ammonium hydrogencarbonate (0.057 g; 0.724 mmol) was added and the reaction mixture was stirred 12 h at room temperature. Methylene chloride (20 ml) was added and the reaction mixture was washed with sodium hydrogencarbonate (10%; 10 ml), sodium hydrogensulfate (5%; 2×10 ml) and dried (magnesium sulfate). The solvent was removed in vacuo and the residue was chromatographed on silica (2×15 cm) using ethyl acetate/heptane (1:1) as eluent to afford 0.155 g of 2-((1R)-1-(tert-butoxycarbonylamino)-2-(2-naphthyl)ethyl)-5-phenyl-1,3-thiazole-4-carboxylic acid amide.

Provenance & Evidence