Sodium Carbonate → HCID 59363823, compound

HRID 1430635Notes

Reaction equation

HRID 1430635 reaction equation
[CH2:1]([O:3][C:4](=[O:16])[C:5]([O:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([NH2:15])[CH:10]=1)([CH3:7])[CH3:6])[CH3:2].C([O-])([O-])=O.[Na+].[Na+].I[CH2:24][CH2:25][C:26]1[CH:31]=[CH:30][C:29]([C:32]([F:35])([F:34])[F:33])=[CH:28][CH:27]=1>C(#N)C>[CH2:1]([O:3][C:4](=[O:16])[C:5]([CH3:7])([O:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([NH:15][CH2:24][CH2:25][C:26]2[CH:27]=[CH:28][C:29]([C:32]([F:33])([F:34])[F:35])=[CH:30][CH:31]=2)[CH:10]=1)[CH3:6])[CH3:2]

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 184025491-(2-Iodoethyl)-4-(trifluoromethyl)benzeneHCID 22060556HCID 22060556, compound

Product 1

HCID 59363823HCID 59363823, compoundYield 43.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 2-(3-Amino-phenoxy)-2-methyl-propionic acid ethyl ester (0.25 g, 1.11 mmol) in acetonitrile (5 ml), Na2CO3 (0.131 g, 1.24 mmol) and 1-(2-Iodo-ethyl)-4-trifluoromethyl-Benzene (0.372 g, 1.24 mmol) were added. The reaction mixture was stirred at r. t for 3 days, solvent was removed under reduced pressure and extracted in Ethyl acetate (75 ml) and washed with brine (2×10 ml) dried over Na2SO4. After evaporation, the residue was purified by flash chromatography (1:5 ethyl acetate:hexanes) to give 2-Methyl-2-{3-[2-(4-trifluoromethyl-phenyl)-ethylamino]-phenoxy}-propionic acid ethyl ester (0.19 g, 43%).

Workup

  1. customsolvent was removed under reduced pressure
  2. extractionextracted in Ethyl acetate (75 ml)
  3. washwashed with brine (2×10 ml)
  4. dry with materialdried over Na2SO4
  5. customAfter evaporation
  6. customthe residue was purified by flash chromatography (1:5 ethyl acetate:hexanes)

Sources & evidence

ORD record
ord-d84b4fe444bb4a599b3d9e5d7b720829
Source dataset
uspto-grants-2015_01
Patent number
US08940900B2

Reaction notes

Loading…