Hydrogen Peroxide → HCID 68028189, compound

Participants

Reaction Conditions

Reaction Steps

To a 3-necked RBF is added tetrahydrofuran (4.2 L) and water (0.8 L). (4S)-4-benzyl-3-(2-(benzyloxy)-3-(4-(trifluoromethyl)phenyl)propanoyl)oxazolidin-2-one (250 g; 616.65 mmoles) is added and the solution cooled to 0° C. Hydrogen peroxide (4.93 moles; 500.30 mL) is added dropwise over 45 min LiOH (1.08 moles; 45.28 g) in 1.2 L water is added dropwise over 1 h. The resulting mixture is then stirred at 2° C. for 1 h. Sodium Sulfite (2.47 moles; 310.90 g) is dissolved in 2 L of water, and the resulting solution added to the reaction mixture dropwise over 1 h. Upon completion of the addition, the mixture is washed with DCM (2×2 L; 1 L×1). The aqueous phase is then acidified with concentrated HCl (100 ml) to pH=1. The resulting suspension is extracted with EA (2 L×2). The organic extracts are combined, washed with Na2SO3 solution (2 L×1) and brine I (2 L×1), dried over Na2SO4, and filtered to afford the title compound (140 g, MS:[M+H]+=247 m/z) cl Step 4: Synthesis of (2R)—N-[[(4R)-4-cyclopropyl-2,5-dioxo-imidazolidin-4-yl]methyl]-2-[[4-(trifluoromethyl)phenyl]methyl]butanamide (Example 2)

Provenance & Evidence