Potassium Carbonate → HCID 45605619, compound

HRID 1041896Notes

Reaction equation

HRID 1041896 reaction equation
Br[CH2:2][C:3]1[CH:4]=[C:5]([CH:10]=[CH:11][CH:12]=1)[C:6]([O:8][CH3:9])=[O:7].[Br:13][C:14]1[CH:15]=[C:16]([C:20]2([CH3:27])[NH:24][C:23](=[O:25])[NH:22][C:21]2=[O:26])[CH:17]=[CH:18][CH:19]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[CH3:9][O:8][C:6](=[O:7])[C:5]1[CH:10]=[CH:11][CH:12]=[C:3]([CH2:2][N:22]2[C:21](=[O:26])[C:20]([C:16]3[CH:17]=[CH:18][CH:19]=[C:14]([Br:13])[CH:15]=3)([CH3:27])[NH:24][C:23]2=[O:25])[CH:4]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 2433325-(3-bromo-phenyl)-5-methyl-imidazolidine-2,4-dioneHCID 517981Methyl 3-(bromomethyl)benzoate

Product 1

HCID 45605619HCID 45605619, compoundYield 107.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In analogy to the literature (Moloney et al., J. Med. Chem. 1997, 40, 2347-2362), methyl 3-bromomethylbenzoate (4.75 g, 20.7 mmol) was added to a suspension of hydantoin 1 (5.0 g, 18.6 mmol) and potassium carbonate (3.1 g, 22.5 mmol) in DMF (75 mL) at 23° C. After 18 h, the reaction mixture was partitioned between water and EtOAc, and the aqueous layer extracted with EtOAc. The combined organic layers were washed with water (1×), NaHCO3 (1×), water (1×), brine (1×), then dried over MgSO4. After filtration, concentration in vacuo gave an oil, which was subjected to silica gel chromatography (20→50% EtOAc/hexanes) to yield the desired material as a white sticky foam (8.32 g, 100%). 1H NMR (400 MHz, CDCl3) δ 7.92 (m, 2H), 7.58 (m, 1H), 7.34-7.46 (m, 4H), 7.20 (m, 2H), 4.66 (s, 2H), 3.84 (s, 3H), 1.76 (s, 3H).

Workup

  1. customthe reaction mixture was partitioned between water and EtOAc
  2. extractionthe aqueous layer extracted with EtOAc
  3. washThe combined organic layers were washed with water (1×), NaHCO3 (1×), water (1×), brine (1×)
  4. dry with materialdried over MgSO4
  5. filtrationAfter filtration, concentration in vacuo
  6. customgave an oil, which

Sources & evidence

ORD record
ord-64b7fe4eba7a43849cc9965505cb661f
Source dataset
uspto-grants-2013_10
Patent number
US08557798B2

Reaction notes

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