Hydrogen Peroxide → HCID 68768818, compound

HRID 2265228Notes

Reaction equation

HRID 2265228 reaction equation
C([C@@H]1COC(=O)N1[C:14](=[O:26])[C@H:15]([CH3:25])[C@H:16]([C:18]1[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][CH:19]=1)[OH:17])C1C=CC=CC=1.OO.[Li+].[OH-].[O-:31]S([O-])=O.[Na+].[Na+]>O.C1COCC1.O>[Cl:24][C:21]1[CH:20]=[CH:19][C:18]([C@H:16]([OH:17])[C@@H:15]([CH3:25])[C:14]([OH:26])=[O:31])=[CH:23][CH:22]=1

Participants

7

Reactant 4

HCID 784Hydrogen PeroxideHCID 3939Lithium HydroxideHCID 24437Sodium SulfiteHCID 68770794HCID 68770794, compound

Product 1

HCID 68768818HCID 68768818, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 21881883Oxolane--water (1/1)Solvent

Conditions

Temperature
0 °C

Procedure

A solution of (4R)-4-benzyl-3-[(2R,3R)-3-(4-chloro-phenyl)-3-hydroxy-2-methyl-propionyl]-oxazolidin-2-one (1.32 g, 3.53 mmol) in 4:1 THF/water (20 mL) was cooled to 0° C. and treated with 30% aq. H2O2 (1.5 mL, 13.2 mmol) and LiOH (1 M in water, 5.6 mL, 5.6 mmol). The reaction mixture was stirred for 1 h at 0° C., and then a solution of Na2SO3 (1.76 g, 14 mmol) in water (10 mL) was added. The mixture was concentrated at a temperature<30° C. The aqueous layer was extracted with DCM (3×), then was acidified with conc. HCl and extracted with EtOAc (4×). The combined EtOAc layers were dried (Na2SO4) and concentrated to give the crude acid, which was used without further purification (0.76 g, quant.). 1H NMR (500 MHz, CDCl3): 7.36-7.32 (m, 2H), 7.32-7.28 (m, 2H), 5.16 (d, J=3.9, 1H), 2.81 (dq, J=7.2, 3.9, 1H), 1.15 (d, J=7.2, 3H).

Workup

  1. concentrationThe mixture was concentrated at a temperature<30° C
  2. extractionThe aqueous layer was extracted with DCM (3×)
  3. extractionextracted with EtOAc (4×)
  4. dry with materialThe combined EtOAc layers were dried (Na2SO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-68e8e4b6a0df465a81e46ab806fd474a
Source dataset
uspto-grants-2010_12
Patent number
US07855292B2

Reaction notes

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