Potassium Carbonate → 2-(4-{3-[1-(3,4-Dimethyl-benzyl)-2,5-dioxo-imidazolidin-4-yl]-propyl}-phenoxy)-2-methyl-propionic acid tert-butyl ester

HRID 1985245

Reaction equation

HRID 1985245 reaction equation
[C:1]([O:5][C:6](=[O:27])[C:7]([O:10][C:11]1[CH:16]=[CH:15][C:14]([CH2:17][CH2:18][CH2:19][CH:20]2[C:24](=[O:25])[NH:23][C:22](=[O:26])[NH:21]2)=[CH:13][CH:12]=1)([CH3:9])[CH3:8])([CH3:4])([CH3:3])[CH3:2].[CH3:28][C:29]1[CH:30]=[C:31]([CH:34]=[CH:35][C:36]=1[CH3:37])[CH2:32]Cl.[O-]S([O-])(=O)=O.[Mg+2].C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[C:1]([O:5][C:6](=[O:27])[C:7]([O:10][C:11]1[CH:16]=[CH:15][C:14]([CH2:17][CH2:18][CH2:19][CH:20]2[C:24](=[O:25])[N:23]([CH2:32][C:31]3[CH:34]=[CH:35][C:36]([CH3:37])=[C:29]([CH3:28])[CH:30]=3)[C:22](=[O:26])[NH:21]2)=[CH:13][CH:12]=1)([CH3:9])[CH3:8])([CH3:2])([CH3:3])[CH3:4]

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 24083Sulfuric acid magnesium salt (1:1)HCID 660183,4-Dimethylbenzyl chlorideHCID 577189222-{4-[3-(2,5-Dioxo-imidazolidin-4-yl)-propyl]-phenoxy}-2-methyl-propionic acid tert-butyl ester

Product 1

HCID 577190872-(4-{3-[1-(3,4-Dimethyl-benzyl)-2,5-dioxo-imidazolidin-4-yl]-propyl}-phenoxy)-2-methyl-propionic acid tert-butyl esterYield 53%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Compound 2-{4-[3-(2,5-dioxo-imidazolidin-4-yl)-propyl]-phenoxy}-2-methyl-propionic acid tert-butyl ester (0.29 g, 0.770 mmol) in DMF (10 mL) was treated with 3,4-dimethyl benzyl chloride (0.131 g, 0.847 mmol), MgSO4 (0.185 g, 1.54 mmol) and then 325 mesh K2CO3 (0.213 g, 1.54 mmol). The resultant mixture was heated to 50° C. under N2 for 4 h. The reaction mixture was cooled and quenched with 1N HCl (8 mL) and then extracted with EtOAc and water. The organic layer was dried (MgSO4) and the solvent was removed in vacuo to give a crude product which was purified by flash chromatography using a gradient of 4:1 then 1:1 hexanes:EtOAc to afford 0.202 g (53%) 2-(4-{3-[1-(3,4-dimethyl-benzyl)-2,5-dioxo-imidazolidin-4-yl]-propyl}-phenoxy)-2-methyl-propionic acid tert-butyl ester. MS (ES+) Calc'd for C29H39N2O5 (M+1) 495. Found m/z 495 (100%). 1H NMR.

Workup

  1. temperatureThe reaction mixture was cooled
  2. customquenched with 1N HCl (8 mL)
  3. extractionextracted with EtOAc and water
  4. dry with materialThe organic layer was dried (MgSO4)
  5. customthe solvent was removed in vacuo
  6. customto give a crude product which
  7. customwas purified by flash chromatography

Sources & evidence

ORD record
ord-734868c9c4e345aaa51151885a371aba
Source dataset
uspto-grants-2009_06
Patent number
US07544812B2

Linked notes

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