Methanol → HCID 59135088, compound

HRID 1994536Notes

Reaction equation

HRID 1994536 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C@H:9]([OH:16])[C@@H:10]([NH:12][C:13](=[O:15])[O-])[CH3:11])[CH:5]=[C:6]([F:8])[CH:7]=1.CO.[OH-].[K+]>C1COCC1>[F:8][C:6]1[CH:5]=[C:4]([C@@H:9]2[O:16][C:13](=[O:15])[NH:12][C@H:10]2[CH3:11])[CH:3]=[C:2]([F:1])[CH:7]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 14797Potassium HydroxideHCID 86603418HCID 86603418, compound

Product 1

HCID 59135088HCID 59135088, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of [(1S,2S)-2-(3,5-difluorophenyl)-2-hydroxy-1-methylethyl]carbamate (900 mg, 2.80 mmol) in THF (28.6 mL) was added MeOH (14.3 mL) and 7.5 N KOH (7.2 mL). The reaction was stirred at room temperature for 4 hours and then extracted with EtOAc (2×75 mL). The organic extracts were washed with water and brine (50 mL each), dried over Na2SO4, filtered, and concentrated. Purification of the residue by flash chromatography on silica gel (10 to 75% EtOAc/hexanes) afforded (4S,5S)-5-(3,5-difluorophenyl)-4-methyl-1,3-oxazolidin-2-one. Rf=0.07 (25% EtOAc/hexanes). LCMS=214.3 (M+1)+. 1H NMR (CDCl3, 500 MHz) δ 6.89-6.93 (m, 2H), 6.82 (m, 1H), 6.24 (bs, 1H), 5.01 (d, J=6.8 Hz, 1H), 3.79 (m, 1H), 1.42 (d, J=6.2 Hz, 3H).

Workup

  1. extractionextracted with EtOAc (2×75 mL)
  2. washThe organic extracts were washed with water and brine (50 mL each)
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customPurification of the residue by flash chromatography on silica gel (10 to 75% EtOAc/hexanes)

Sources & evidence

ORD record
ord-fd93e02d5d0a4d2e97946aaae78bea69
Source dataset
uspto-grants-2010_01
Patent number
US07652049B2

Reaction notes

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