Potassium Carbonate → HCID 57719025, compound

HRID 1985228Notes

Reaction equation

HRID 1985228 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([CH:26]=[CH:27][C:28]=1[CH3:29])[CH2:5][N:6]1[C:10]([CH3:11])=[C:9]([CH2:12][CH2:13][CH2:14][C:15]2[CH:20]=[CH:19][C:18]([OH:21])=[CH:17][CH:16]=2)[N:8]([CH2:22][CH2:23][CH3:24])[C:7]1=[O:25].Br[C:31]([CH3:38])([CH3:37])[C:32]([O:34][CH2:35][CH3:36])=[O:33].[O-]S([O-])(=O)=O.[Mg+2].C([O-])([O-])=O.[K+].[K+]>C(O)C>[CH2:35]([O:34][C:32](=[O:33])[C:31]([O:21][C:18]1[CH:17]=[CH:16][C:15]([CH2:14][CH2:13][CH2:12][C:9]2[N:8]([CH2:22][CH2:23][CH3:24])[C:7](=[O:25])[N:6]([CH2:5][C:4]3[CH:26]=[CH:27][C:28]([CH3:29])=[C:2]([CH3:1])[CH:3]=3)[C:10]=2[CH3:11])=[CH:20][CH:19]=1)([CH3:38])[CH3:37])[CH3:36]

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 11745Propanoic acid, 2-bromo-2-methyl-, ethyl esterHCID 24083Sulfuric acid magnesium salt (1:1)HCID 68869787HCID 68869787, compound

Product 1

HCID 57719025HCID 57719025, compoundYield 69%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
75 °C

Procedure

The crude 1-(3,4-dimethyl-benzyl)-4-[3-(4-hydroxy-phenyl)-propyl]-5-methyl-3-propyl-1,3-dihydro-imidazol-2-one (0.169 g) was combined with ethyl 2-bromoisobutyrate (0.366 g, 1.87 mmol), MgSO4 (0.043 g, 0.357 mmol) and 325 mesh K2CO3 (0.197 g, 1.43 mmol) in ethanol (8 mL) and heated a 75° C. for 16 h under N2. The reaction was cooled and the solvent removed in vacuo. The residue was acidified with 1 N HCl (10 mL) and extracted with EtOAc and water. The organic layer was dried (MgSO4), and the solvent removed in vacuo to afford crude product that was purified by flash chromatography using 2:1 to hexanes:acetone to afford 0.124 g (69%) 2-(4-{3-[1-(3,4-dimethyl-benzyl)-5-methyl-2-oxo-3-propyl-2,3-dihydro-1H-imidazol-4-yl]-propyl}-phenoxy)-2-methyl-propionic acid ethyl ester. MS (ES+) Calc'd for C31H43N2O4 (M+1) 507. Found m/z 507 (100%). 1H NMR.

Workup

  1. temperatureThe reaction was cooled
  2. customthe solvent removed in vacuo
  3. extractionextracted with EtOAc and water
  4. dry with materialThe organic layer was dried (MgSO4)
  5. customthe solvent removed in vacuo
  6. customto afford crude product that
  7. customwas purified by flash chromatography

Sources & evidence

ORD record
ord-bd1404cc263a4c1ba69fd7d77f5bafba
Source dataset
uspto-grants-2009_06
Patent number
US07544812B2

Reaction notes

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