Potassium Hydroxide → HCID 178464364, compound

HRID 505294Notes

Reaction equation

HRID 505294 reaction equation
[F:1][C:2]([F:49])([F:48])[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]([O:26][C:27]([F:30])([F:29])[F:28])[CH:23]=[CH:22][C:21]=3[N:31]([CH2:34][C@H:35]3[CH2:40][CH2:39][C@H:38]([CH2:41][C:42]([O:44]CC)=[O:43])[CH2:37][CH2:36]3)[CH2:32][CH3:33])[C@H:14]2[CH3:47])[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1.[OH-].[K+]>CCO>[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[CH:25]=[C:24]([O:26][C:27]([F:29])([F:30])[F:28])[CH:23]=[CH:22][C:21]=3[N:31]([CH2:34][C@H:35]3[CH2:36][CH2:37][C@H:38]([CH2:41][C:42]([OH:44])=[O:43])[CH2:39][CH2:40]3)[CH2:32][CH3:33])[C@H:14]2[CH3:47])[CH:4]=[C:3]([C:2]([F:1])([F:49])[F:48])[CH:8]=1

Participants

4

Reactant 2

HCID 14797Potassium Hydroxide3×HCID 178471789HCID 178471789, compound

Product 1

HCID 178464364HCID 178464364, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of ethyl (trans-4-{[[2-({(4S,5R)-5-[3,5-bis(trifluoromethyl)phenyl]-4-methyl-2-oxo-1,3-oxazolidin-3-yl}methyl)-4-(trifluoromethoxy)phenyl](ethyl)amino]methyl}cyclohexyl)acetate (29 mg, 0.0407 mmol) in EtOH (1 mL) was added 4 M KOH (100 μL). The reaction was stirred at room temperature for 30 minutes and 4 M KOH (100 μL) was added. After an additional 30 minutes 4 M KOH (100 μL) was added. After 30 min the reaction was quenched with 1 N HCl (1.5 mL) and then neutralized with saturated NaHCO3 solution. The mixture was extracted with EtOAc (2×20 mL) and washed with brine. The organic layer was dried over Na2SO4, filtered, and concentrated. Purification of the residue by PTLC (EtOAc+1% AcOH) afforded (trans-4-{[[2-({(4S,5R)-5-[3,5-bis(trifluoromethyl)phenyl]-4-methyl-2-oxo-1,3-oxazolidin-3-yl}methyl)-4-(trifluoromethoxy)phenyl](ethyl)amino]methyl}cyclohexyl)acetic acid. Rf=0.94 (EtOAc+1% AcOH). LCMS=685.3 (M+1)+. 1H NMR (CDCl3, 500 MHz) δ 7.91 (s, 1H), 7.80 (s, 2H), 7.20-7.12 (m, 3H), 5.76 (d, J=8.1 Hz, 1H), 4.74 (d, J=16.3 Hz, 1H), 4.59 (d, J=16.3 Hz, 1H), 4.04-4.00 (m, 1H), 2.97-2.75 (m, 4H), 1.81-0.88 (m, 15H), 0.66 (d, J=6.5 Hz, 3H).

Workup

  1. customAfter 30 min the reaction was quenched with 1 N HCl (1.5 mL)
  2. extractionThe mixture was extracted with EtOAc (2×20 mL)
  3. washwashed with brine
  4. dry with materialThe organic layer was dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customPurification of the residue by PTLC (EtOAc+1% AcOH)

Sources & evidence

ORD record
ord-c62861f6acb045408f66330bb9f925b0
Source dataset
uspto-grants-2010_08
Patent number
US07781426B2

Reaction notes

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