Hydrogen Peroxide → HCID 69070503, compound

HRID 228134Notes

Reaction equation

HRID 228134 reaction equation
O=C1C=CC=CC1C[C@@H]1COCN1[C:10](=[O:28])[C@@H:11]([CH2:20][C:21]1[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][CH:22]=1)[CH2:12][C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14].[OH:33]O.O[Li].O>C1COCC1>[C:16]([O:15][C:13]([CH2:12][C@H:11]([CH2:20][C:21]1[CH:22]=[CH:23][C:24]([Cl:27])=[CH:25][CH:26]=1)[C:10]([OH:28])=[O:33])=[O:14])([CH3:17])([CH3:18])[CH3:19]

Participants

5

Reactant 3

HCID 784Hydrogen PeroxideHCID 168937Lithium hydroxide, monohydrateHCID 69078142HCID 69078142, compound

Product 1

HCID 69070503HCID 69070503, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of tert-butyl 4-[(4R)-2-oxo-4-benzyl-(1,3-oxazolidin-3-yl)](3S)-3-[(4-chlorophenyl)methyl]-4-oxobutanoate (Step 3) (0.3 g, 0.656 mmol) in 10 mL of THF was added 0.1 mL of H2O2 (35%) and 33 mg of LiOH—H2O (0.787 mmol). The reaction was stirred at RT for 3 h and extracted with 30 mL of Et2O. The aqueous solution was acidified with 2N HCl to pH˜2 and extracted with 50 mL of EtOAc. These EtOAc extractions were combined, dried over Na2SO4 and concentrated in vacuo. (2S)-3-[(tert-Butyl)-oxycarbonyl]-2-[(4-chlorophenyl)methyl]-propanoic acid was obtained as light yellow oil (0.15 g) and was used in the next step without further purification. MS (ESI, pos. ion) m/z: 299.0 (M+1). Calc'd for C15H19ClO4: 298.10.

Workup

  1. extractionextracted with 30 mL of Et2O
  2. extractionextracted with 50 mL of EtOAc
  3. extractionThese EtOAc extractions
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-2a54e3688fcf483cb1b578639ef9fa60
Source dataset
uspto-grants-2009_07
Patent number
US07560460B2

Reaction notes

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