Methanol → HCID 59135088, compound

HRID 1028566Notes

Reaction equation

HRID 1028566 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-e353195f0b7d4f8181c14e993060e5b7
Source dataset
uspto-grants-2014_05
Patent number
US08735435B2

Reaction notes

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