Potassium Carbonate → (2S)-3-(4-Cyano-3-fluorophenoxy)-N-(4-cyano-3-methylphenyl)-2-hydroxy-2-methylpropionamide

HRID 1888365Notes

Reaction equation

HRID 1888365 reaction equation
[F:1][C:2]1[CH:9]=[C:8]([OH:10])[CH:7]=[CH:6][C:3]=1[C:4]#[N:5].[C:11]([C:13]1[CH:18]=[CH:17][C:16]([NH:19][C:20]([C@@:22]2([CH3:25])[CH2:24][O:23]2)=[O:21])=[CH:15][C:14]=1[CH3:26])#[N:12].C([O-])([O-])=O.[K+].[K+]>CCOC(C)=O>[C:4]([C:3]1[CH:6]=[CH:7][C:8]([O:10][CH2:25][C@@:22]([OH:23])([CH3:24])[C:20]([NH:19][C:16]2[CH:17]=[CH:18][C:13]([C:11]#[N:12])=[C:14]([CH3:26])[CH:15]=2)=[O:21])=[CH:9][C:2]=1[F:1])#[N:5]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 27346752-Fluoro-4-hydroxybenzonitrileHCID 86761994(2R)-2-Methyloxirane-2-carboxylicacid-(4-cyano-3-methylphenyl)amide

Product 1

HCID 16730514(2S)-3-(4-Cyano-3-fluorophenoxy)-N-(4-cyano-3-methylphenyl)-2-hydroxy-2-methylpropionamideYield 70.8%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Conditions

Temperature
50 °C

Procedure

2-Fluoro-4-hydroxy benzonitrile (0.81 g, 5.9 mmol) and (2R)-2-methyl-oxirane-2-carboxylicacid-(4-cyano-3-methylphenyl)amide (0.905 g, 4.2 mmol) were dissolved in 17.6 ml of EtOAc. Anhydrous K2CO3 (0.29 g; 2.1 mmol) was added and the mixture heated to 50° C. and stirred for 25.5 hours. The mixture was cooled to room temperature, 30 ml of EtOAc added and washed first with 2×24 ml of 1M Na2CO3 and then 2×24 ml of water. Organic layer was dried over Na2SO4, filtered and evaporated to give 1.05 g of crude product.

Workup

  1. temperatureThe mixture was cooled to room temperature
  2. washwashed first with 2×24 ml of 1M Na2CO3
  3. dry with materialOrganic layer was dried over Na2SO4
  4. filtrationfiltered
  5. customevaporated

Sources & evidence

ORD record
ord-af42ce5cc59043e3a520d25c011156bf
Source dataset
uspto-grants-2013_08
Patent number
US08501814B2

Reaction notes

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