Hydrochloric Acid → HCID 67099182, compound

Participants

Reaction Steps

Oxalyl chloride (2.9 mL, 34 mmol) was added dropwise to a −78° C. solution of dimethyl sulfoxide (2.9 mL, 41 mmol) in CH2Cl2 (40 mL). Stirring was continued at −78° C. for an additional 10 min prior to the slow introduction down the flask wall of a solution of ethyl 3-{2-[(benzyloxy)methyl]-4,4-difluorocyclohexyl}-3-hydroxy-2-[4-(methylthio)phenyl]propanoate (5.09 g, 10.6 mmol) and triethylamine (16 mL, 120 mmol) in CH2Cl2 (40 mL). The mixture was then held at −78° C. for 10 min followed by rapid warming to rt before being poured into 2 M HCl in a separatory funnel. The layers were shaken and separated, and the aqueous phase was extracted with an additional portion of CH2Cl2. The combined organics were washed with water, dried (Na2SO4) and concentrated. Flash chromatography of the residue on silica gel eluting with 1/4 ethyl acetate/hexanes afforded ethyl 3-{2-[(benzyloxy)methyl]-4,4-difluorocyclohexyl}-2-[4-(methylthio)phenyl]-3-oxopropanoate as a thick, tan colored syrup.

Provenance & Evidence