Sodium Hydroxide → 4-Cyano-3-(4-fluorophenyl)-4-(3-fluorophenyl)butanoic acid
Reaction equation
[OH-].[Na+].[C:3]([CH:5]([C:19]1[CH:24]=[CH:23][CH:22]=[C:21]([F:25])[CH:20]=1)[CH:6]([C:12]1[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=1)[CH2:7][C:8]([O:10]C)=[O:9])#[N:4]>CO>[C:3]([CH:5]([C:19]1[CH:24]=[CH:23][CH:22]=[C:21]([F:25])[CH:20]=1)[CH:6]([C:12]1[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=1)[CH2:7][C:8]([OH:10])=[O:9])#[N:4]Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 25 °C
Procedure
Under protective gas (Ar), 10 ml of 2 molar aqueous sodium hydroxide solution were added to 1.75 g (5.55 mmol) of methyl 4-cyano-3-(4-fluorophenyl)-4-(3-fluorophenyl)butanoate (Example A1) in 50.0 ml of methanol, and the mixture was stirred at 25° C. for 8 h. The methanol was removed under reduced pressure. The residue was acidified with concentrated hydrochloric acid (pH=3) and extracted three times with in each case 15 ml of dichloromethane. The combined organic phases were dried over sodium sulphate and the solvent was removed under reduced pressure. This gave 1.62 g (96.9% of theory) of the title compound in the form of colourless crystals (erythro:threo=49:51 according to comparison of the multiplets in the 1H-NMR in CDCl3 at 2.60 and 2.85 ppm).
Workup
- customThe methanol was removed under reduced pressure
- extractionextracted three times with in each case 15 ml of dichloromethane
- dry with materialThe combined organic phases were dried over sodium sulphate
- customthe solvent was removed under reduced pressure
Sources & evidence
- ORD record
- ord-7f22207b2d484ef7a7b0b3848a1a5021
- Source dataset
- uspto-grants-2015_07
- Patent number
- US09084425B2
Reaction notes
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