HCID 88439250, compound → HCID 67814081, compound

Participants

Reaction Conditions

Reaction Steps

To a round bottomed flask was added (R,E)-N-((4-(2-(4-chlorobenzoyl)phenyl)-3-methylisoxazol-5-yl)methylene)-2-methylpropane-2-sulfinamide (0.083 g, 0.194 mmol) in THF (0.5 mL). This solution was cooled to 0° C. before addition of (2-tert-butoxy-2-oxoethyl)zinc(II) chloride (0.464 mL, 0.232 mmol) and stirring at 0° C. for 1 h before addition of another more zinc reagent (0.388 mL, 0.194 mmol). After stirring 3 h at 0° C. the solution was quenched with aqueous ammonium chloride solution and EtOAc added. The layers were separated and the aqueous extracted with EtOAc. The combined organics were washed with brine, dried over Na2SO4, filtered and concentrated. The crude residue was purified via Biotage (EtOAc/hex) to afford (3S)-tert-butyl 3-(4-(2-(4-chlorobenzoyl)phenyl)-3-methylisoxazol-5-yl)-3-((R)-1,1-dimethylethylsulfinamido)propanoate (Rf (1:1 EtOAc:hex)=˜0.3, Mass: 0.043 g, LC/MS m/z 545 [M+H]+) and (3R)-tert-butyl 3-(4-(2-(4-chlorobenzoyl)phenyl)-3-methylisoxazol-5-yl)-3-((R)-1,1-dimethylethylsulfinamido)propanoate (Rf (1:1 EtOAc:hex)=˜0.15, Mass: 0.045 g, LC/MS m/z 545 [M+H]+).

Provenance & Evidence