Hydrogen Peroxide → HCID 69877110, compound

HRID 1860039Notes

Reaction equation

HRID 1860039 reaction equation
[O-]S(C(F)(F)F)(=O)=O.C([B+]CCCC)CCC.[CH2:18]([C@H:25]1[CH2:29][O:28][C:27](=[O:30])[N:26]1[C:31](=[O:43])[CH2:32][O:33][C:34]1[CH:39]=[CH:38][C:37]([CH:40]([CH3:42])[CH3:41])=[CH:36][CH:35]=1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.[CH2:44]([O:51][C:52]1[CH:59]=[CH:58][C:55]([CH:56]=[O:57])=[CH:54][CH:53]=1)[C:45]1[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=1.[Cl-].[Na+].OO>ClCCl.C(N(CC)CC)C.CO>[CH2:18]([C@H:25]1[CH2:29][O:28][C:27](=[O:30])[N:26]1[C:31](=[O:43])[C@@H:32]([O:33][C:34]1[CH:39]=[CH:38][C:37]([CH:40]([CH3:41])[CH3:42])=[CH:36][CH:35]=1)[C@@H:56]([C:55]1[CH:58]=[CH:59][C:52]([O:51][CH2:44][C:45]2[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=2)=[CH:53][CH:54]=1)[OH:57])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

9

Reactant 5

HCID 784Hydrogen PeroxideHCID 5234Sodium ChlorideHCID 78109Benzaldehyde, 4-(phenylmethoxy)-HCID 69876187HCID 69876187, compoundHCID 178418657HCID 178418657, compound

Product 1

HCID 69877110HCID 69877110, compoundYield 80.3%

Reagents, catalysts & solvents 3

HCID 887MethanolSolvent2×HCID 6344DichloromethaneSolvent3×HCID 8471TriethylamineSolvent

Procedure

A solution of dibutylboron triflate in dichloromethane (1M, 67.9 ml) and triethylamine (10.2 ml) was added to a solution of (S)-4-benzyl-3-[(4-isopropylphenoxy)acetyl]oxazolidine-2-one (20.0 g) in dichloromethane (150 ml) at 0° C. The mixture was stirred at the same temperature for 1 hour. To the reaction mixture a solution of 4-benzyloxybenzaldehyde (13.2 g) in dichloromethane (20 ml) was added dropwise at −78° C. and then stirred at the same temperature for 40 minutes. The reaction mixture was further stirred at 0° C. for 1 hour. At the end of this time a mixture of saturated aqueous sodium chloride solution/methanol=1/1 (50 ml) and aqueous hydrogen peroxide solution (31%)/methanol=2/1 (150 ml) was added to the reaction mixture and stirred for 1 hour. The mixture was concentrated under reduced pressure. The residue was partitioned between ethyl acetate and water and the layers were separated. The ethyl acetate layer was washed with aqueous hydrogen chloride solution (1N), saturated aqueous sodium hydrogencarbonate solution and saturated aqueous sodium chloride solution and dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified via chromatography on a silica gel column using hexane/ethyl acetate=3/1-1/1 as the eluant to afford the desired compound (25.7 g) as a mass of foam.

Workup

  1. stirringstirred at the same temperature for 40 minutes
  2. stirringThe reaction mixture was further stirred at 0° C. for 1 hour
  3. additionwas added to the reaction mixture
  4. stirringstirred for 1 hour
  5. concentrationThe mixture was concentrated under reduced pressure
  6. customThe residue was partitioned between ethyl acetate and water
  7. customthe layers were separated
  8. washThe ethyl acetate layer was washed with aqueous hydrogen chloride solution (1N), saturated aqueous sodium hydrogencarbonate solution and saturated aqueous sodium chloride solution
  9. dry with materialdried over anhydrous magnesium sulfate
  10. concentrationconcentrated under reduced pressure
  11. customThe residue was purified via chromatography on a silica gel column

Sources & evidence

ORD record
ord-42f6353e16984c9c83dc385651d8ad2b
Source dataset
uspto-grants-2003_03
Patent number
US06528525B1

Reaction notes

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