Tetrabutylammonium Fluoride → HCID 11555615, compound

HRID 1994546Notes

Reaction equation

HRID 1994546 reaction equation
[F:1][C:2]([F:47])([F:46])[C:3]1[CH:4]=[C:5]([C@H:13]2[O:17][C:16](=[O:18])[N:15]([CH2:19][C:20]3[CH:25]=[C:24]([C:26]([F:29])([F:28])[F:27])[CH:23]=[CH:22][C:21]=3[C:30]3[CH:34]=[CH:33][N:32]([Si](C(C)C)(C(C)C)C(C)C)[CH:31]=3)[C@H:14]2[CH3:45])[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1>[F:47][C:2]([F:1])([F:46])[C:3]1[CH:4]=[C:5]([C@H:13]2[O:17][C:16](=[O:18])[N:15]([CH2:19][C:20]3[CH:25]=[C:24]([C:26]([F:29])([F:28])[F:27])[CH:23]=[CH:22][C:21]=3[C:30]3[CH:34]=[CH:33][NH:32][CH:31]=3)[C@H:14]2[CH3:45])[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 86603419HCID 86603419, compound

Product 1

HCID 11555615HCID 11555615, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a 0° C. solution of (4S,5R)-5-[3,5-bis(trifluoromethyl)phenyl]-4-methyl-3-{5-(trifluoromethyl)-2-[1-(triisopropylsilyl)-1H-pyrrol-3-yl]benzyl}-1,3-oxazolidin-2-one (Example 149) (22.6 mg, 0.0326 mmol) in THF (2 mL) was added TBAF (65 μL of a 1M solution in THF, 0.065 mmol). After 30 minutes, the reaction was quenched with saturated NH4Cl (5 mL). The mixture was extracted with EtOAc (35 mL) and the organic layer was washed with water and brine (15 mL each). The organic layer was dried over Na2SO4, filtered, and concentrated. Purification of the residue by flash chromatography on silica gel (25 to 60% EtOAc/hexanes) afforded (4S,5R)-5-[3,5-bis(trifluoromethyl)phenyl]-4-methyl-3-[2-(1H-pyrrol-3-yl)-5-(trifluoromethyl)benzyl]-1,3-oxazolidin-2-one. Rf=0.11 (25% EtOAc/hexanes). LCMS=537.1 (M+1)+. 1H NMR (CDCl3, 600 MHz) δ 8.49 (s, 1H), 7.85 (s, 1H), 7.71 (s, 2H), 7.64 (s, 1H), 7.58 (d, J=8.1 Hz, 1H), 7.51 (d, J=8.0 Hz, 1H), 6.88-6.91 (m, 2H), 6.33 (d, J=1.6 Hz, 1H), 5.53 (d, J=8.0 Hz, 1H), 5.02 (d, J=15.7 Hz, 1H), 4.46 (d, J=15.6 Hz, 1H), 3.80 (m, 1H), 0.49 (d, J=6.6 Hz, 3H).

Workup

  1. customthe reaction was quenched with saturated NH4Cl (5 mL)
  2. extractionThe mixture was extracted with EtOAc (35 mL)
  3. washthe organic layer was washed with water and brine (15 mL each)
  4. dry with materialThe organic layer was dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customPurification of the residue by flash chromatography on silica gel (25 to 60% EtOAc/hexanes)

Sources & evidence

ORD record
ord-f84113e6d1e94f8f8a7e5c8b39900dda
Source dataset
uspto-grants-2010_01
Patent number
US07652049B2

Reaction notes

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