Hydrogen Peroxide → (S)-4-Benzyl-3-[(2S,3R)-3-(4-benzyloxyphenyl)-3-hydroxy-2-(4-methylphenoxy)propionyl]oxazolidin-2-one

HRID 1268946Notes

Reaction equation

HRID 1268946 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:41])[CH2:32][O:33][C:34]1[CH:39]=[CH:38][C:37]([CH3:40])=[CH:36][CH:35]=1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.[CH2:42]([O:49][C:50]1[CH:57]=[CH:56][C:53]([CH:54]=[O:55])=[CH:52][CH:51]=1)[C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=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:41])[C@@H:32]([O:33][C:34]1[CH:39]=[CH:38][C:37]([CH3:40])=[CH:36][CH:35]=1)[C@@H:54]([C:53]1[CH:56]=[CH:57][C:50]([O:49][CH2:42][C:43]2[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=2)=[CH:51][CH:52]=1)[OH:55])[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 69504430(S)-4-Benzyl-3-[(4-methylphenoxy)acetyl]oxazolidin-2-oneHCID 178418657HCID 178418657, compound

Product 1

HCID 69504531(S)-4-Benzyl-3-[(2S,3R)-3-(4-benzyloxyphenyl)-3-hydroxy-2-(4-methylphenoxy)propionyl]oxazolidin-2-oneYield 65.9%

Reagents, catalysts & solvents 3

HCID 887MethanolSolvent2×HCID 6344DichloromethaneSolvent3×HCID 8471TriethylamineSolvent

Conditions

Temperature
0 °C

Procedure

A 1M solution of dibutylboron triflate in dichloromethane (33.2 ml) and triethylamine (5.12 ml) were added at 0° C. to a solution of (S)-4-benzyl-3-[(4-methylphenoxy)acetyl]oxazolidin-2-one (9.00 g) obtained from Reference example 20(a) in dichloromethane (90 ml), and the mixture was stirred at 0° C. for 1 hour. A solution of 4-benzyloxybenzaldehyde (6.46 g) in dichloromethane (6 ml) was added dropwise at −78° C. to the reaction solution, and then the reaction solution was stirred at 0° C. for 2 hours. A mixed solution (20 ml) of a saturated aqueous sodium chloride solution and methanol (1:1) and a mixed solution (100 ml) of an aqueous solution of hydrogen peroxide (31%) and methanol (2:1) were added thereto, and the resulting reaction solution was stirred for 1 hour. After the methanol was evaporated under reduced pressure, the residue was extracted with ethyl acetate. The ethyl acetate layer was washed successively with an aqueous solution of hydrochloric acid (1N), a saturated aqueous sodium hydrogencarbonate solution and a saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by chromatography on a silica gel column (eluant; hexane/ethyl acetate=3/1˜1/1) to afford the target compound (9.80 g) as a foam.

Workup

  1. stirringthe reaction solution was stirred at 0° C. for 2 hours
  2. customthe resulting reaction solution
  3. stirringwas stirred for 1 hour
  4. customAfter the methanol was evaporated under reduced pressure
  5. extractionthe residue was extracted with ethyl acetate
  6. washThe ethyl acetate layer was washed successively with an aqueous solution of hydrochloric acid (1N)
  7. dry with materiala saturated aqueous sodium hydrogencarbonate solution and a saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate
  8. concentrationconcentrated under reduced pressure
  9. customThe residue was purified by chromatography on a silica gel column (eluant; hexane/ethyl acetate=3/1˜1/1)

Sources & evidence

ORD record
ord-40a7555766e843cba8bd935aa0aeef7b
Source dataset
uspto-grants-2007_04
Patent number
US07199139B2

Reaction notes

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