Sodium hydride → (5S)-3-(4-(3,6-Dihydro-2H-pyran-4-yl)-3-fluorophenyl)-5-(2-oxo-1H-pyridin-1-ylmethyl)oxazolidin-2-one

HRID 723794Notes

Reaction equation

HRID 723794 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][N:3]=1.[H-].[Na+].[O:10]1[CH2:15][CH:14]=[C:13]([C:16]2[CH:21]=[CH:20][C:19]([N:22]3[CH2:26][C@H:25]([CH2:27]OS(C)(=O)=O)[O:24][C:23]3=[O:33])=[CH:18][C:17]=2[F:34])[CH2:12][CH2:11]1>CN(C)C=O>[O:10]1[CH2:11][CH:12]=[C:13]([C:16]2[CH:21]=[CH:20][C:19]([N:22]3[CH2:26][C@H:25]([CH2:27][N:3]4[CH:4]=[CH:5][CH:6]=[CH:7][C:2]4=[O:1])[O:24][C:23]3=[O:33])=[CH:18][C:17]=2[F:34])[CH2:14][CH2:15]1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 213566765(R)-methanesulfonyloxymethyl 3-(4-[3,6-dihydro-(2H)-pyran-4-yl]-3-fluorophenyl)oxazolidin-2-oneHCID 178516071HCID 178516071, compound

Product 1

HCID 44354874(5S)-3-(4-(3,6-Dihydro-2H-pyran-4-yl)-3-fluorophenyl)-5-(2-oxo-1H-pyridin-1-ylmethyl)oxazolidin-2-oneYield 28.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2-Hydroxypyridine (108 mg, 1.14 mM) was added at room temperature, under an atmosphere of nitrogen, to a stirred suspension of sodium hydride (60% dispersion in oil, 48 mg, 1.2 mM) in N,N-dimethylformamide (5 ml). The reaction was stirred for 30 minutes then (5R)-3-(4-(3,6-dihydro-2H-pyran-4-yl)-3-fluorophenyl)-5-methanesulfonyloxymethyloxazolidin-2-one (400 mg, 1.08 mM; WO 97-09328) was added in one portion. The mixture was stirred and heated at 60° for 5 hour before quenching in water (20 ml) and extracting with ethyl acetate. The extract was washed twice with water and once with saturated brine, dried (magnesium sulfate) and evaporated to an orange oil, which was purified by flash chromatography on silica, eluting with 2.5% methanol in dichloromethane to give the title compound (115 mg) as a colourless solid.

Workup

  1. stirringThe mixture was stirred
  2. temperatureheated at 60° for 5 hour
  3. custombefore quenching in water (20 ml)
  4. extractionextracting with ethyl acetate
  5. washThe extract was washed twice with water and once with saturated brine
  6. dry with materialdried (magnesium sulfate)
  7. customevaporated to an orange oil, which
  8. customwas purified by flash chromatography on silica
  9. washeluting with 2.5% methanol in dichloromethane

Sources & evidence

ORD record
ord-4cca95dca340460f912052089e70f7ef
Source dataset
uspto-grants-2006_11
Patent number
US07141583B2

Reaction notes

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