Sodium Hydroxide → HCID 57719041, compound

HRID 1985248Notes

Reaction equation

HRID 1985248 reaction equation
[C:1]([C:5]1[CH:28]=[CH:27][C:8]([CH2:9][N:10]2[CH2:14][CH:13]([CH2:15][CH2:16][CH2:17][C:18]3[CH:23]=[CH:22][C:21]([OH:24])=[CH:20][CH:19]=3)[N:12]([CH3:25])[C:11]2=[O:26])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].CC(C)([O-])C.[K+].Br[C:36]([CH2:44][CH3:45])([CH2:42][CH3:43])[C:37]([O:39]CC)=[O:38].[OH-].[Na+]>CC(O)(C)C>[C:1]([C:5]1[CH:28]=[CH:27][C:8]([CH2:9][N:10]2[CH2:14][CH:13]([CH2:15][CH2:16][CH2:17][C:18]3[CH:19]=[CH:20][C:21]([O:24][C:36]([CH2:44][CH3:45])([CH2:42][CH3:43])[C:37]([OH:39])=[O:38])=[CH:22][CH:23]=3)[N:12]([CH3:25])[C:11]2=[O:26])=[CH:7][CH:6]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 14798Sodium HydroxideHCID 237833ETHYL alpha-BROMODIETHYLACETATEHCID 23665647Potassium tert-butoxideHCID 68869042HCID 68869042, compound

Product 1

HCID 57719041HCID 57719041, compoundYield 14%

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 1-(4-tert-butyl-benzyl)-4-[3-(4-hydroxy-phenyl)-propyl]-3-methyl-imidazolidin-2-one (0.077 g, 0.202 mmol), potassium tert-butoxide (0.091 g, 0.745 mmol) and ethyl α-bromodiethylacetate (0.361 g, 1.61 mmol) in 2-methyl-2-propanol (8 mL) was heated to 100° C. under N2 for 16 h. Aqueous 5 N NaOH (1.5 mL) was added to the reaction mixture and it was heated at reflux an additional 1 h. The reaction mixture was cooled and quenched with 1 N HCl. The mixture was then diluted with water and extracted with CH2Cl2. The organic layer was dried (Na2SO4) and the solvent removed in vacuo to afford 0.288 g of crude product that was purified by preparative HPLC to give 0.014 g (14%) 2-(4-{3-[1-(4-tert-butyl-benzyl)-3-methyl-2-oxo-imidazolidin-4-yl]-propyl}-phenoxy)-2-ethyl-butyric acid. 1H NMR. HRMS (ES+) m/z exact mass calcd for C30H43N2O4 [M+1] 495.3223, found 495.3252.

Workup

  1. temperaturewas heated
  2. temperatureat reflux an additional 1 h
  3. temperatureThe reaction mixture was cooled
  4. customquenched with 1 N HCl
  5. additionThe mixture was then diluted with water
  6. extractionextracted with CH2Cl2
  7. dry with materialThe organic layer was dried (Na2SO4)
  8. customthe solvent removed in vacuo
  9. customto afford 0.288 g of crude product that
  10. customwas purified by preparative HPLC

Sources & evidence

ORD record
ord-ee644e56f9964a2aad72740238b25019
Source dataset
uspto-grants-2009_06
Patent number
US07544812B2

Reaction notes

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