Sodium Hydroxide → HCID 57633744, compound

HRID 2240885Notes

Reaction equation

HRID 2240885 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([N:9]([CH2:17][C:18]([F:21])([F:20])[F:19])[CH2:10][CH:11]([CH3:16])[C:12]([O:14]C)=[O:13])=[CH:5][C:4]=1[C:22]([F:25])([F:24])[F:23])#[N:2].[OH-].[Na+]>C1COCC1.CO>[C:1]([C:3]1[CH:8]=[CH:7][C:6]([N:9]([CH2:17][C:18]([F:21])([F:19])[F:20])[CH2:10][CH:11]([CH3:16])[C:12]([OH:14])=[O:13])=[CH:5][C:4]=1[C:22]([F:23])([F:25])[F:24])#[N:2]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 57633720HCID 57633720, compound

Product 1

HCID 57633744HCID 57633744, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Conditions

Temperature
75 °C

Procedure

A solution of methyl 3-[[4-cyano-3-(trifluoromethyl)phenyl](2,2,2-trifluoroethyl)amino]-2-methylpropanoate (0.056 g, 0.152 mmol) in 1:1 THF/MeOH (6 mL) was treated with NaOH (1N, 1 mL, 1.0 mmol) and heated at 75° C. for 30 min. Upon cooling, the mixture was partitioned between EtOAc and 0.1N HCl. The aqueous phase was extracted with EtOAc and the combined organic phases were washed with brine, dried (Na2SO4) and concentrated in vacuo to give the title compound (0.050 g, 94% yield): 1H NMR (400 MHz, CDCl3) δ 7.66 (d, J=8.8 Hz, 1H), 7.06 (d, J=2.6 Hz, 1H), 6.92 (dd, J=8.8, 2.6 Hz, 1H), 4.20-4.02 (m, 2H), 3.87 (dd, J=15.6, 9.0 Hz, 1H), 3.56 (dd, J=15.6, 5.0 Hz, 1H), 3.0-2.9 (m, 1H), 1.29 (d, J=7.1 Hz, 3H).

Workup

  1. temperatureUpon cooling
  2. customthe mixture was partitioned between EtOAc and 0.1N HCl
  3. extractionThe aqueous phase was extracted with EtOAc
  4. washthe combined organic phases were washed with brine
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-8d83bd1ab9134edba0d1c8486c840670
Source dataset
uspto-grants-2010_05
Patent number
US07723385B2

Reaction notes

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