4-Methylmorpholine → HCID 54450617, compound

Participants

Reaction Steps

A mixture of 5-bromothiophene-2-carboxylic acid (3.1 g, 15 mmol), 2-benzenesulfonylamino-2-tert-butoxycarbonyl-ethyl-ammonium chloride (4.58 g, 13.6 mmol), 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide hydrochloride (2.87 g, 15 mmol), 1-hydroxybenzotriazole (2.01 g, 15 mmol) and 4-methylmorpholine (3 mL, 27.3 mmol) in dry dimethylformamide (DMF, 36 mL) was stirred at room temperature for 16 h. The DMF was removed and the mixture was dissolved in ethyl acetate (400 mL), washed with water (25 mL), saturated NaCl solution (25 mL), 5% KHSO4 (25 mL), saturated NaCl solution (25 mL) and saturated NaHCO3-saturated NaCl mixture (1:1) (25 mL), dried and evaporated. The crude was passed through a column of silica gel with CH2Cl2-acetone (95:5 and 90:10) as eluents yielding 6 g of compound A-1(90% yield).

Provenance & Evidence