Hydrochloric Acid → HCID 67814706, compound

Participants

Reaction Steps

To a round bottomed flask was added methyl 5-chloro-2-(5-((S)-1-((S)-1,1-dimethylethylsulfinamido)ethyl)-3-methylisoxazol-4-yl)benzoate (3.37 g, 8.45 mmol), MeOH (48 mL), and HCl [2M in ether] (8.45 mL, 16.90 mmol). The reaction was stirred at room temperature for 30 min before concentrating. The crude residue was concentrated from toluene (2×) and hexane (1×) before being placed on a high vacuum line overnight. The crude residue (as an off-white foam) was dissolved in THF (100 mL) before cooling to −78° C. and addition of isopropylmagnesium chloride (15 mL, 30.0 mmol). The solution was stirred at −78° C. for 5 min before removal of the cold bath and warming the reaction to room temperature. The solution was quenched with saturated aqueous NH4Cl and diluted with EtOAc. The layers were separated and the aqueous layer was extracted with EtOAc. The combined organic layers were washed with brine, dried over Na2SO4, filtered, and concentrated to afford a white solid. This material was purified via chiral SFC to afford the titled compound (1.9 g, 7.23 mmol); LC/MS m/z 263 [M+H]+.

Provenance & Evidence