Sodium Hydroxide → HCID 86628111, compound

HRID 2245246Notes

Reaction equation

HRID 2245246 reaction equation
[F:1][C:2]([F:40])([F:39])[C:3]1[CH:4]=[C:5]([C@H:13]([O:15][C@H:16]2[CH2:21][CH2:20][C@H:19]([C:22]([O:24]CC)=[O:23])[C@@H:18]([C:27]([O:29][CH2:30][CH3:31])=[O:28])[C@@H:17]2[C:32]2[CH:37]=[CH:36][C:35]([F:38])=[CH:34][CH:33]=2)[CH3:14])[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1.[OH-].[Na+]>CO>[F:39][C:2]([F:1])([F:40])[C:3]1[CH:4]=[C:5]([C@H:13]([O:15][C@H:16]2[CH2:21][CH2:20][C@H:19]([C:22]([OH:24])=[O:23])[C@@H:18]([C:27]([O:29][CH2:30][CH3:31])=[O:28])[C@@H:17]2[C:32]2[CH:33]=[CH:34][C:35]([F:38])=[CH:36][CH:37]=2)[CH3:14])[CH:6]=[C:7]([C:9]([F:10])([F:11])[F:12])[CH:8]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 42639483HCID 42639483, compound

Product 1

HCID 86628111HCID 86628111, compoundYield 94.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Diethyl (1S,2S,3R,4S)-4-{(1R)-1-[3,5-bis(trifluoromethyl)phenyl]ethoxy}-3-(4-fluorophenyl)cyclohexane-1,2-dicarboxylate (3.0 g, 5.19 mmol, intermediate from Example 1, Step 1) was dissolved 50 mL methanol. NaOH (20 mL, 5 N) was added at room temperature. The mixture was stirred for 20 hr. Solvent methanol and water were removed under vacuum. The residue was dissolved in 100 mL 2N aq. HCl. The aqueous layer was extracted with ethyl acetate (2×100 mL). The combined organic extracts were washed with brine, dried over MgSO4, filtered and the solvent was removed under vacuum to give the title compound (2.7 g). 1H-NMR (CDCl3) δ: 7.71 (1H, s), 7.21 (2H, s), 6.98 (2H, m), 6.85 (2H, m), 4.43 (1H, q, J=6.4 Hz), 3.75 (2H, q, J=7.1 Hz), 3.35 (1H, m), 2.92-2.72 (3H, m), 2.38 (1H, m), 2.30 (1H, m), 1.60 (2H, m), 1.33 (3H, d, J=6.4 Hz), 0.80 (3H, t, J=7.1 Hz).

Workup

  1. customSolvent methanol and water were removed under vacuum
  2. dissolutionThe residue was dissolved in 100 mL 2N aq. HCl
  3. extractionThe aqueous layer was extracted with ethyl acetate (2×100 mL)
  4. washThe combined organic extracts were washed with brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. customthe solvent was removed under vacuum

Sources & evidence

ORD record
ord-c9e34133f3824b279f5e7fed4304f291
Source dataset
uspto-grants-2010_03
Patent number
US07683068B2

Reaction notes

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