Hydrogen Peroxide → 4-(1-(4-Bromobenzyl)-5-methoxy-2-methyl-1H-indol-3-yl)-3-methylbutanoic acid

Participants

Reaction Conditions

Reaction Steps

To the oxazolidinone from Step 7, isomer A (295 mg, 0.54 mmol) in THF (10 mL) at -10° C. was added 30% H2O2 (0.5 mL) followed by 1M aqueous LiOH (3 mL). The mixture was stirred at 0° C. for 45 min, and was then cooled to -10° C. to be quenched by careful addition of 1M aqueous Na2S2O5 (10 mL). The mixture was acidified (6M HCl, 1 mL) and the product was extracted with EtOAc. The organic layer was washed with H2O and brine, and was then dried (MgSO4), and filtered. After removal of the solvent, the crude product was purified by flash chromatography (1:5 EtOAc/hexane followed by 1:2 EtOAc/hexane). The resulting off-white solid was stirred vigorously with 1:10 EtOAc/hexane for 2 h to give, after filtration, 188 mg of the title compound. [α]D =+4.6° (c=1, acetone)

Provenance & Evidence