HCID 24969647, compound → HCID 24969731, compound

HRID 604644Notes

Reaction equation

HRID 604644 reaction equation
[F:1][C:2]([F:43])([F:42])[C:3]1[CH:4]=[C:5]([C@H:13]2[O:17][C:16](=[O:18])[N:15]([CH2:19][C:20]3[C:25]([C:26]4[CH:31]=[C:30]([CH:32]([CH3:34])[CH3:33])[C:29]([F:35])=[CH:28][C:27]=4[O:36][CH3:37])=[CH:24][CH:23]=[C:22]([C:38]([CH3:40])=[CH2:39])[N:21]=3)[C@H:14]2[CH3:41])[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1.[H][H]>CCO.[Pd]>[F:12][C:9]([F:10])([F:11])[C:7]1[CH:6]=[C:5]([C@H:13]2[O:17][C:16](=[O:18])[N:15]([CH2:19][C:20]3[C:25]([C:26]4[CH:31]=[C:30]([CH:32]([CH3:34])[CH3:33])[C:29]([F:35])=[CH:28][C:27]=4[O:36][CH3:37])=[CH:24][CH:23]=[C:22]([CH:38]([CH3:40])[CH3:39])[N:21]=3)[C@H:14]2[CH3:41])[CH:4]=[C:3]([C:2]([F:1])([F:42])[F:43])[CH:8]=1

Participants

5

Reactant 2

HCID 24969647HCID 24969647, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 24969731HCID 24969731, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution of (4S,5R)-5-[3,5-bis(trifluoromethyl)phenyl]-3-{[3-(4-fluoro-5-isopropyl-2-methoxyphenyl)-6-isopropenylpyridin-2-yl]methyl}-4-methyl-1,3-oxazolidin-2-one (20 mg, 0.033 mmol) in anhydrous EtOH (3 mL), was added a catalytic amount of 10% of palladium on carbon. The mixture was stirred under 1 atm of hydrogen for 2 h. The reaction mixture was filtered through Celite. The solvent was concentrated in vacuo. Flash chromatography of the residue (Si, hexanes/EtOAc) afforded (4S,5R)-5-[3,5-bis(trifluoromethyl)phenyl]-3-{[3-(4-fluoro-5-isopropyl-2-methoxyphenyl)-6-isopropylpyridin-2-yl]methyl}-4-methyl-1,3-oxazolidin-2-one. LCMS calc.=613.2; found=613.3 (M+1)+. 1H NMR (500 MHz, CDCl3, 1:1 mixture of atropisomers): δ 7.88 (s, 1H); 7.75 (s, 2H); 7.45 (d, J=7.8 Hz, 1H); 7.17 (d, J=7.8 Hz, 1H); 7.04 (br, s, 0.5H); 6.98 (br, s, 0.5H); 6.70 (s, 0.5H); 6.68 (s, 0.5H); 5.72-5.56 (br, m, 1H); 4.95-4.76 (br, m, 1H); 4.41 (br, m, 0.5H); 4.23 (br, m, 0.5H); 4.18-3.89 (br, m, 1H); 3.77 (s, 3H); 3.25-3.19 (m, 1H); 3.16-3.08 (m, 1H); 1.37 (m, 6H); 1.28 (d, J=6.9 Hz, 6H); 0.73 (br, s, 1.5H); 0.62 (br, s, 1.5H).

Workup

  1. filtrationThe reaction mixture was filtered through Celite
  2. concentrationThe solvent was concentrated in vacuo

Sources & evidence

ORD record
ord-bb120d5aacb344e7b4866fa29d7a2b73
Source dataset
uspto-grants-2011_03
Patent number
US07910592B2

Reaction notes

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