Lithium Hydroxide → HCID 59363821, compound

HRID 1430636Notes

Reaction equation

HRID 1430636 reaction equation
C([O:3][C:4](=[O:28])[C:5]([CH3:27])([O:7][C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([NH:14][CH2:15][CH2:16][C:17]2[CH:22]=[CH:21][C:20]([C:23]([F:26])([F:25])[F:24])=[CH:19][CH:18]=2)[CH:9]=1)[CH3:6])C.[Li+].[OH-]>C1COCC1.O>[CH3:27][C:5]([O:7][C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([NH:14][CH2:15][CH2:16][C:17]2[CH:18]=[CH:19][C:20]([C:23]([F:24])([F:26])[F:25])=[CH:21][CH:22]=2)[CH:9]=1)([CH3:6])[C:4]([OH:28])=[O:3]

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 59363823HCID 59363823, compound

Product 1

HCID 59363821HCID 59363821, compoundYield 33.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-Methyl-2-{3-[2-(4-trifluoromethyl-phenyl)-ethylamino]-phenoxy}-propionic acid ethyl ester (0.24 g, 0.608 mmol) in THF (15 ml) was added a solution of LiOH (0.127 g, 3.03 mmol) in water (3.4 ml) and stirred at r.t. for 18 h. After evaporation of the solvent, the residue was diluted with ethyl acetate (100 ml); cool to 0° C., acidified with 1N HCl (pH˜3-4). The organic phase were washed with, brine (20 ml) and dried over Na2SO4 and concentrated to get 2-Methyl-2-{3-[2-(4-trifluoromethyl-phenyl)-ethylamino]-phenoxy}-propionic acid (0.075 g, 33%). 1H NMR (400 MHz, CDCl3): δ 1.588 (s, 6H), 2.97 (t, J=6.8 Hz, 2H), 3.41 (t, J=6.8 Hz, 2H), 6.22 (s, 1H), 6.30 (d, J=8.4 Hz, 1H), 6.37 (d, J=8 Hz, 1H), 7.08 (t, J=8.0 Hz, 1H), 7.32 (d, J=8 Hz, 2H), 7.57 (d, J=7.6 Hz, 2H).

Workup

  1. customAfter evaporation of the solvent
  2. additionthe residue was diluted with ethyl acetate (100 ml)
  3. temperaturecool to 0° C.
  4. washThe organic phase were washed with, brine (20 ml)
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-35531a7b7cb242bcbd99da939a44a79d
Source dataset
uspto-grants-2015_01
Patent number
US08940900B2

Reaction notes

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