Hydrogen Peroxide → HCID 68028189, compound

HRID 1500233Notes

Reaction equation

HRID 1500233 reaction equation
C([C@H]1COC(=O)N1[C:14](=[O:35])[CH:15](OCC1C=CC=CC=1)[CH2:16][C:17]1[CH:22]=[CH:21][C:20]([C:23]([F:26])([F:25])[F:24])=[CH:19][CH:18]=1)C1C=CC=CC=1.[OH:36]O.[Li+].[OH-].S([O-])([O-])=O.[Na+].[Na+].O1CC[CH2:48][CH2:47]1>O>[F:26][C:23]([F:24])([F:25])[C:20]1[CH:19]=[CH:18][C:17]([CH2:16][C@@H:15]([CH2:47][CH3:48])[C:14]([OH:35])=[O:36])=[CH:22][CH:21]=1

Participants

7

Reactant 5

HCID 784Hydrogen PeroxideHCID 3939Lithium HydroxideHCID 8028TetrahydrofuranHCID 24437Sodium SulfiteHCID 90111942HCID 90111942, compound

Product 1

HCID 68028189HCID 68028189, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent3×

Conditions

Temperature
0 °C

Procedure

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)

Workup

  1. additionis added dropwise over 1 h
  2. additionthe resulting solution added to the reaction mixture dropwise over 1 h
  3. additionUpon completion of the addition
  4. washthe mixture is washed with DCM (2×2 L; 1 L×1)
  5. extractionThe resulting suspension is extracted with EA (2 L×2)
  6. washwashed with Na2SO3 solution (2 L×1) and brine I (2 L×1)
  7. dry with materialdried over Na2SO4
  8. filtrationfiltered

Sources & evidence

ORD record
ord-30f15a531af44462b4dab4e42d0953b3
Source dataset
uspto-grants-2015_12
Patent number
US09206139B2

Reaction notes

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