Sodium hydride → HCID 86704606, compound

HRID 1508516Notes

Reaction equation

HRID 1508516 reaction equation
[F:1][C:2]([F:21])([F:20])[C:3]1[CH:4]=[C:5]([C@H:13]2[O:17][C:16](=[O:18])[NH:15][C@H:14]2[CH3:19])[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1.[H-].[Na+].[Cl:24][C:25]1[C:26]([CH3:38])=[N:27][C:28]([S:36][CH3:37])=[N:29][C:30]=1[CH2:31]S(C)(=O)=O.[NH4+].[Cl-]>C1COCC1>[F:21][C:2]([F:1])([F:20])[C:3]1[CH:4]=[C:5]([C@H:13]2[O:17][C:16](=[O:18])[N:15]([CH2:31][C:30]3[C:25]([Cl:24])=[C:26]([CH3:38])[N:27]=[C:28]([S:36][CH3:37])[N:29]=3)[C@H:14]2[CH3:19])[CH:6]=[C:7]([C:9]([F:10])([F:11])[F:12])[CH:8]=1

Participants

6

Reactant 4

HCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 23583229(4S,5R)-5-(3,5-bis(trifluoromethyl)phenyl)-4-methyloxazolidin-2-oneHCID 77230708HCID 77230708, compound

Product 1

HCID 86704606HCID 86704606, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

A solution of (4S,5R)-5-[3,5-bis(trifluoromethyl)phenyl]-4-methyl-1,3-oxazolidin-2-one (614 mg, 1.961 mmol) in THF (20 mL) was cooled to 0° C. NaH (58.8 mg, 2.451 mmol) was added. The mixture was stirred at 0° C. for 30 min. The title compound from Step E (462 mg, 1.63 mmol) in THF (30 mL) was added. The mixture was stirred at 0° C. and then room temperature for 4 h. Saturated NH4Cl (10 mL) was added. The mixture was extracted with ethyl acetate (3×10 mL). The combined organic fractions were washed with brine (saturated, 10 mL), dried (Na2SO4), filtered and the solvent was evaporated under reduced pressure. The residue was purified by column chromatography on silica gel Biotage 40S, eluting with EtOAc/hexane (30/70) to give the title compound as a colorless solid. 1H NMR (CDCl3, 500 MHz) δ 7.94 (s, 1H), 7.82 (s, 2H), 5.85 (d, J=8.5 Hz, 1H), 5.00 (d, J=17.5 Hz, 1H), 4.46 (m, 1H), 4.31 (d, J=18.0 Hz, 1H), 2.60 (s, 6H), 0.83 (d, J=7.0 Hz, 3H).

Workup

  1. stirringThe mixture was stirred at 0° C.
  2. waitroom temperature for 4 h
  3. extractionThe mixture was extracted with ethyl acetate (3×10 mL)
  4. washThe combined organic fractions were washed with brine (saturated, 10 mL)
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. customthe solvent was evaporated under reduced pressure
  8. customThe residue was purified by column chromatography on silica gel Biotage 40S
  9. washeluting with EtOAc/hexane (30/70)

Sources & evidence

ORD record
ord-5f167861417440f29cfa4aaddaf39aed
Source dataset
uspto-grants-2015_12
Patent number
US09221834B2

Reaction notes

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