Lithium Hydroxide → HCID 89782773, compound

HRID 877446Notes

Reaction equation

HRID 877446 reaction equation
[CH3:1][S:2]([C:5]1[CH:6]=[C:7]([C:11]2[CH:16]=[CH:15][C:14]([C:17]3[N:21]([CH2:22][C:23]([O:25]CC)=[O:24])[N:20]=[C:19]([C:28]([F:31])([F:30])[F:29])[CH:18]=3)=[CH:13][CH:12]=2)[CH:8]=[CH:9][CH:10]=1)(=[O:4])=[O:3].[OH-].[Li+]>C1COCC1.O>[CH3:1][S:2]([C:5]1[CH:6]=[C:7]([C:11]2[CH:16]=[CH:15][C:14]([C:17]3[N:21]([CH2:22][C:23]([OH:25])=[O:24])[N:20]=[C:19]([C:28]([F:31])([F:29])[F:30])[CH:18]=3)=[CH:13][CH:12]=2)[CH:8]=[CH:9][CH:10]=1)(=[O:3])=[O:4]

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 89792952Ethyl 2-[5-[3′-(methylsulfonyl)biphenyl-4-yl]-3-(trifluoromethyl)-1H-pyrazol-1-yl]acetate

Product 1

HCID 89782773HCID 89782773, compoundYield 117.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 36 (1.3 g, 2.0 mmol) in THF (10.0 mL) at room temperature, was added a solution of lithium hydroxide (103 mg, 4.0 mmol) in water (10.0 mL) and stirring continued for 2 h. On completion, the solvent was removed and the reaction mixture diluted with water (20 mL) and washed with ether (30 mL×3). The aqueous layer was acidified with 1N HCl and extracted with 10% methanol in dichloromethane (50 mL×3). Combined organic layer was washed brine, dried over sodium sulphate and concentrated. The crude product after ether and pentane washing afforded 38 (1 g, 83%). LCMS: 425.15 (M+1)+; 1H NMR (DMSO-ds, 400 MHz) δ 13.3 (s, 1H), 8.24 (s, 2H), 8.12 (d, 1H, J=8 Hz), 7.78 (t, 1H, J=8 Hz), 7.67 (d, 1H, J=8.4 Hz), 7.04 (s, 1H), 5.13 (s, 1H), 3.25 (s, 3H).

Workup

  1. customOn completion, the solvent was removed
  2. additionthe reaction mixture diluted with water (20 mL)
  3. washwashed with ether (30 mL×3)
  4. extractionextracted with 10% methanol in dichloromethane (50 mL×3)
  5. washCombined organic layer was washed brine
  6. dry with materialdried over sodium sulphate
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-830d3af01b484880b8ced041f50b6fbd
Source dataset
uspto-grants-2015_03
Patent number
US08987318B2

Reaction notes

Loading…