Methanol → HCID 68869975, compound

HRID 1985273Notes

Reaction equation

HRID 1985273 reaction equation
[C:1]([C:5]1[CH:35]=[CH:34][C:8]([CH2:9][N:10]2[CH2:14][CH:13]([CH2:15][CH2:16][CH2:17][C:18]3[CH:30]=[CH:29][C:21]([O:22][C:23]([CH3:28])([CH3:27])[C:24]([OH:26])=[O:25])=[C:20]([CH3:31])[CH:19]=3)[N:12]([CH3:32])[C:11]2=[O:33])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[CH3:36]O>S(=O)(=O)(O)O>[CH3:36][O:25][C:24](=[O:26])[C:23]([O:22][C:21]1[CH:29]=[CH:30][C:18]([CH2:17][CH2:16][CH2:15][CH:13]2[CH2:14][N:10]([CH2:9][C:8]3[CH:34]=[CH:35][C:5]([C:1]([CH3:2])([CH3:3])[CH3:4])=[CH:6][CH:7]=3)[C:11](=[O:33])[N:12]2[CH3:32])=[CH:19][C:20]=1[CH3:31])([CH3:27])[CH3:28]

Participants

4

Reactant 2

HCID 887MethanolHCID 10195632HCID 10195632, compound

Product 1

HCID 68869975HCID 68869975, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidCatalyst

Procedure

To a solution of 2-(4-{3-[1-(4-tert-Butyl-benzyl)-3-methyl-2-oxo-imidazolidin-4-yl]-propyl}-2-methyl-phenoxy)-2-methyl-propionic acid (0.610 g, 1.27 mmole) in methanol (10 mL) was added 15 drops of concentrated sulfuric acid. The mixture was stirred at room temperature overnight. After evaporated the solvent, the residue was partitioned between ethyl acetate (50 mL) and water (50 mL). The organic layer was washed by saturated sodium bicarbonate (50 mL), then brine (3×50 mL), dried over Na2SO4, filtered and concentrated in vacuo to produce an oil (0.624 g, 99%). Mass [EI+] 495 (M+H)+.

Workup

  1. customAfter evaporated the solvent
  2. customthe residue was partitioned between ethyl acetate (50 mL) and water (50 mL)
  3. washThe organic layer was washed by saturated sodium bicarbonate (50 mL)
  4. dry with materialbrine (3×50 mL), dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-2f91848927b448c1b084eb0b03b2558e
Source dataset
uspto-grants-2009_06
Patent number
US07544812B2

Reaction notes

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