Hydrogen Peroxide → HCID 68292485, compound

Participants

Reaction Conditions

Reaction Steps

To a round bottom flask was added (2S,3E,5S)-2-benzyl-1,6-bis((7aS)-8,8-dimethyl-2,2-dioxidotetrahydro-3a,6-methano-2,1-benzothiazol-1(3H,4H)-yl)-5-(2-methylpropyl)hex-3-ene-1,6-dione (54 mg, 0.079 mmol), THF (1 mL) and water (0.35 mL). The reaction was cooled to 0° C. and a solution of H2O2 (50% in water, 0.038 mL, 0.63 mmol) was added to the reaction mixture followed by LiOH monohydrate (13.2 mg, 0.315 mmol). The reaction was stirred at 0° C. for 35 min. The reaction was quenched by addition of saturated Na2SO3 (0.4 mL) and saturated NaHCO3 (0.4 mL). The mixture was concentrated to remove most of the THF. The mixture was diluted with a small amount of water and extracted with EtOAc (2×) to remove the chiral auxiliary. The aqueous phase was then acidified and extracted with EtOAc (2×). The organic extracts were combined, dried over MgSO4, filtered and concentrated to give (2S,5S,E)-2-benzyl-5-isobutylhex-3-enedioic acid (15 mg, 0.052 mmol, 66% yield) as a colorless solid.

Provenance & Evidence