Potassium Carbonate → HCID 54277533, compound

HRID 2396801Notes

Reaction equation

HRID 2396801 reaction equation
Br[CH2:2][C:3]#[N:4].C(=O)([O-])[O-].[K+].[K+].[NH2:11][C@@H:12]([C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)[CH2:13][O:14][CH2:15][C:16]1[CH:21]=[C:20]([C:22]([F:25])([F:24])[F:23])[CH:19]=[C:18]([C:26]([F:29])([F:28])[F:27])[CH:17]=1>CN(C=O)C>[F:29][C:26]([F:27])([F:28])[C:18]1[CH:17]=[C:16]([CH2:15][O:14][CH2:13][C@@H:12]([NH:11][CH2:2][C:3]#[N:4])[C:30]2[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=2)[CH:21]=[C:20]([C:22]([F:24])([F:25])[F:23])[CH:19]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 11534BromoacetonitrileHCID 22859115HCID 22859115, compound

Product 1

HCID 54277533HCID 54277533, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Bromoacetonitrile (570 μl) was stirred in a 0.5M solution of anhydrous DMF (15ml) at 60° C. with potassium carbonate (2.07g) for 5 minutes before (S)-2-amino-1-((3,5-bis(trifluoromethyl) phenyl)methyloxy)-2-phenylethane (2.7g, Example 2b, liberated from the salt by extraction into ethyl acetate from aqueous Na2CO3 solution) was added. After 1.5 hours, the solution was cooled and the reaction quenched with water (100ml) and diluted with Ethyl acetate (60ml). The mixture was separated and the aqueous layer further extracted with ethyl acetate (4×30ml). The combined organic extracts were washed with brine (1×30ml), dried (MgSO4) and evaporated to a dark oil (4.1g). The crude oil was purified by flash silica gel chromatography in Ethyl acetate/hexane (1:1) to yield (S)-1-((3,5-bis(trifluoromethyl)phenyl)methyloxy)-2-cyanomethylamino-2-phenylethane as a viscous oil 2.5g. 1H NMR (250MHz, CDCl3) δ 7.82 (1H, s, Ar), 7.79 (2H, s, ArH), 7.36 (5H, m, Ph), 4.67 (2H, s, OCH2Ar), 4.27 (1H, t, J=6.5Hz, PhCHN), 3.68 (1H, d, J=17Hz) and 3.31 (1H, d, J=17Hz, CH2CN). m/z (CI+) 403 (M+1, 100%).

Workup

  1. extractionliberated from the salt by extraction into ethyl acetate from aqueous Na2CO3 solution)
  2. additionwas added
  3. temperaturethe solution was cooled
  4. customthe reaction quenched with water (100ml)
  5. additiondiluted with Ethyl acetate (60ml)
  6. customThe mixture was separated
  7. extractionthe aqueous layer further extracted with ethyl acetate (4×30ml)
  8. washThe combined organic extracts were washed with brine (1×30ml)
  9. dry with materialdried (MgSO4)
  10. customevaporated to a dark oil (4.1g)
  11. customThe crude oil was purified by flash silica gel chromatography in Ethyl acetate/hexane (1:1)

Sources & evidence

ORD record
ord-4188d34a962343f0b354b97e17771eb8
Source dataset
uspto-grants-1996_02
Patent number
US05494926

Reaction notes

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