Acetyl chloride → HCID 59223144, compound

Participants

Reaction Steps

To a stirred solution of 15 (15 mg, 19 μmol) in CH2Cl2 (0.8 mL) was added Et3SiH (16 μL, 0.1 mmol) and TFA (0.2 mL). After stirring at room temperature for 30 minutes under an inert atmosphere, the reaction mixture was concentrated and the residue dried by high vacuum. Without further purification, the crude thiol 16 was used in next step. At 0° C., to a stirred solution of thiol 16 in CH2Cl2 (0.3 mL) was added DIPEA (17 μL, 0.1 mmol) and AcCl (2 μL, 28 □mol). After 30 minutes the reaction mixture was warmed to rt and stirred for a further 1.5 h, whereupon it was quenched by addition of 1M HCl (1 mL). EtOAc (5 mL) was added to dilute the solution, phases separated, and the aqueous phase extracted with EtOAc (2×1 mL). The combined organic phases were washed with sat. aq NaCl (2 mL), dried (MgSO4), filtered, and concentrated in vacuo. The residue was purified by flash chromatography (eluent: 1-10% IPA/CH2Cl2) to give compound 17 (5 mg, 8 μmol, 45%) as an off white solid.

Provenance & Evidence