Sodium Hydroxide → HCID 67482740, compound

HRID 1817772Notes

Reaction equation

HRID 1817772 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([F:11])([F:10])[F:9])=[CH:4][C:3]=1[C:12]1[CH:16]=[C:15]([C:17]2[CH:26]=[CH:25][C:24]3[C:19](=[CH:20][CH:21]=[C:22]([O:27][CH3:28])[CH:23]=3)[CH:18]=2)[N:14]([C@H:29]([C:31]2[CH:41]=[CH:40][C:34]([C:35]([O:37]CC)=[O:36])=[CH:33][CH:32]=2)[CH3:30])[N:13]=1.[OH-].[Na+]>CO.O1CCOCC1.O>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([F:11])([F:10])[F:9])=[CH:4][C:3]=1[C:12]1[CH:16]=[C:15]([C:17]2[CH:26]=[CH:25][C:24]3[C:19](=[CH:20][CH:21]=[C:22]([O:27][CH3:28])[CH:23]=3)[CH:18]=2)[N:14]([C@H:29]([C:31]2[CH:32]=[CH:33][C:34]([C:35]([OH:37])=[O:36])=[CH:40][CH:41]=2)[CH3:30])[N:13]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 67482849HCID 67482849, compound

Product 1

HCID 67482740HCID 67482740, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 21966525Dioxane MethanolSolvent

Procedure

Ethyl 4-{(1S)-1-[3-[2-fluoro-5-(trifluoromethyl)phenyl]-5-(6-methoxy-2-naphthyl)-1H-pyrazol-1-yl]ethyl}benzoate (2.87 g, 5.11 mmol) was dissolved in MeOH-dioxane (1:2, 60 ml) and treated with NaOH (2.5 g, excess) in water (20 ml). The mixture slowly cleared with stirring, and was left overnight. The reaction mixture was first concentrated to ˜30 ml, acidified with 2N HCl and extracted with ethyl acetate. The organic layer was washed with brine 2× and dried over Na2SO4. Evaporation of solvent and vacuum drying afforded 4-{(1S)-1-[3-[2-fluoro-5-(trifluoromethyl)phenyl]-5-(6-methoxy-2-naphthyl)-1H-pyrazol-1-yl]ethyl}benzoic acid as colorless dry foam. NMR (500 MHz, CDCl3) δ: 2.00 (d, J=7.0 Hz, 3H); 3.95 (s, 3H); 5.65 (q, J=7.0 Hz, 1H); 6.88 (d, JF-H=4.2 Hz, 1H); 7.17 (d, J=2.5 Hz, 1H); 7.20 (dd, J=2.5 Hz, 8.9 Hz, 1H); 7.26 (t, J=8.6 Hz, 1H); 7.31 (dd, J=1.8 Hz, 8.5 Hz, 1H); 7.32 (d, J=8.4 Hz, 2H); 7.56 (m, 1H); 7.66 (d, J=1.8 Hz, 1H); 7.68 (d, J=8.9 Hz, 1H); 7.77 (d, J=8.5 Hz, 1H); 8.06 (d, J=8.4 Hz, 2H); 8.48 (dd, J=2.9 Hz, 6.9 Hz, 1H). MS C30H22F4N2O3 Cald: 534.16; Obsd (M+1): 535.17.

Workup

  1. concentrationThe reaction mixture was first concentrated to ˜30 ml
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with brine 2×
  4. dry with materialdried over Na2SO4
  5. customEvaporation of solvent and vacuum
  6. customdrying

Sources & evidence

ORD record
ord-fccff8b6ebd6401f92e978f69841dfe5
Source dataset
uspto-grants-2009_10
Patent number
US07598285B2

Reaction notes

Loading…