Hydrochloric Acid → HCID 57719306, compound

HRID 1985244Notes

Reaction equation

HRID 1985244 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][CH2:10][CH:11]2[CH2:15][N:14]([CH2:16][C:17]3[CH:22]=[CH:21][C:20]([CH3:23])=[CH:19][CH:18]=3)[C:13](=[O:24])[N:12]2[CH2:25][CH2:26][CH3:27])=[CH:4][CH:3]=1.Br[C:29]([CH3:36])([CH3:35])[C:30]([O:32][CH2:33][CH3:34])=[O:31].[O-]S([O-])(=O)=O.[Mg+2].C([O-])([O-])=O.[K+].[K+].N#N.Cl>C(O)C.CCOC(C)=O>[CH2:33]([O:32][C:30](=[O:31])[C:29]([CH3:36])([O:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][CH2:10][CH:11]2[CH2:15][N:14]([CH2:16][C:17]3[CH:18]=[CH:19][C:20]([CH3:23])=[CH:21][CH:22]=3)[C:13](=[O:24])[N:12]2[CH2:25][CH2:26][CH3:27])=[CH:4][CH:3]=1)[CH3:35])[CH3:34]

Participants

9

Reactant 6

HCID 313Hydrochloric AcidHCID 947NitrogenHCID 11430Potassium CarbonateHCID 11745Propanoic acid, 2-bromo-2-methyl-, ethyl esterHCID 24083Sulfuric acid magnesium salt (1:1)HCID 57719312HCID 57719312, compound

Product 1

HCID 57719306HCID 57719306, compoundYield 72.1%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 4-[3-(4-hydroxy-phenyl)-propyl]-1-(4-methyl-benzyl)-3-propyl-imidazolidin-2-one (0.687 g, 1.87 mmol), ethyl 2-bromoisobutyrate (2.55 g, 13.1 mmol), MgSO4 (0.22 g, 1.83 mmol) and 325 mesh K2CO3 (0.77 g, 5.57 mmol) in ethanol (60 mL) was heated at 70° C. for under N2 for 16 h. The reaction mixture was cooled and the solvent removed in vacuo to give a residue that was acidified with 1 N HCl (20 mL). The reaction was diluted with EtOAc and washed with water. The organic layer was dried (MgSO4) and the solvent removed in vacuo to give crude product that was purified by flash chromatography using 5:1 hexanes:acetone to afford 0.648 g (72%) 2-methyl-2-(4-{3-[1-(4-methyl-benzyl)-2-oxo-3-propyl-imidazolidin-4-yl]-propyl}-phenoxy)-propionic acid ethyl ester. MS (ES+) Calc'd for C29H41N2O4 (M+1) 481. Found m/z 481 (100%). 1H NMR.

Workup

  1. temperatureThe reaction mixture was cooled
  2. customthe solvent removed in vacuo
  3. customto give a residue that
  4. washwashed with water
  5. dry with materialThe organic layer was dried (MgSO4)
  6. customthe solvent removed in vacuo
  7. customto give crude product that
  8. customwas purified by flash chromatography

Sources & evidence

ORD record
ord-4981615bd04e4bcca4c92369b31345fd
Source dataset
uspto-grants-2009_06
Patent number
US07544812B2

Reaction notes

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