Triethylamine → HCID 11814324, compound

Participants

Reaction Steps

To an ice cold solution of Example 9G (1.096 g, 1.72 mmol) in CH2Cl2 (12 mL) under N2 was added DMF (5 drops) and oxalyl chloride (0.30 mL, 3.45 mmol), and the reaction was allowed to stir at room temperature for 1 hour. The solvent was then removed by rotary evaporation chasing with anhydrous toluene (5 mL), and the residue was taken up in CH2Cl2 (7 mL) and added to a 0° C. solution of hydroxylamine hydrochloride (1.21 g, 0.017 mol) and triethylamine (2.9 mL, 0.021 mol) in THF/H20 (2:1 v/v, 12 mL). After allowing the reaction mixture to stir at room temperature for 3 hours, ethyl acetate (100 mL) and H2O (25 mL) were added, the layers were separated, and the organic phase was washed with 1 M HCl (2×10 mL), saturated aqueous NaHCO3 (10 mL), brine, dried (Na2SO4), filtered, and concentrated. The residue was triturated with CH2Cl2 (75 mL) and vacuum filtered to remove a solid impurity. The filtrate was concentrated and the residue purified on silica gel (1.9×6 cm) with a gradient of CH2Cl2 to 3% MeOH/CH2Cl2 +0.5% concentrated NH4OH to obtain 0.459 g (410%) of the desired compound as light beige solid.

Provenance & Evidence