Ethyl Acetate → HCID 20089208, compound

HRID 274925Notes

Reaction equation

HRID 274925 reaction equation
[H-].[Na+].[NH:3]1[C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=2[NH:5][C:4]1=[O:12].[C:13]([CH:17]([C:33]1[CH:38]=[CH:37][CH:36]=[C:35]([CH3:39])[CH:34]=1)[O:18][C:19]1[C:26]([CH2:27][CH2:28][CH3:29])=[CH:25][C:22]([CH2:23]Br)=[CH:21][C:20]=1[CH2:30][CH2:31][CH3:32])([O:15][CH3:16])=[O:14].[C:40](OCC)(=O)C>CN(C=O)C>[C:13]([CH:17]([C:33]1[CH:38]=[CH:37][CH:36]=[C:35]([CH3:39])[CH:34]=1)[O:18][C:19]1[C:26]([CH2:27][CH2:28][CH3:29])=[CH:25][C:22]([CH2:23][N:3]2[C:7]3[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=3[NH:5][C:4]2=[O:12])=[CH:21][C:20]=1[CH2:30][CH2:31][CH3:32])([O:15][CH2:16][CH3:40])=[O:14]

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 119852-Hydroxy benzimidazoleHCID 24758Sodium hydrideHCID 20089198HCID 20089198, compound

Product 1

HCID 20089208HCID 20089208, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a suspention of 4 mg (0.17 mmol) of sodium hydride in 1.0 mL of DMF was added 75 mg (0.17 mmol) of (3H)-benzimidazolone and the reaction mixture was stirred for 20 minutes. 75 mg (0.17 mmol) of 4-(1-carbomethoxy-1-(3-methylphenyl)methoxy)-3,5-dipropylbenzylbromide in 1.0 mL of DMF was added and the reaction mixture was stirred at room is temperature overnight. The reaction mixture was poured into ethyl acetate and washed with water and then brine. The organic layer was dried over sodium sulfate, decanted and concentrated. Purification by flash chromatography (silica gel, hexane/ethyl acetate 2:1) provided 41 mg of a dialkylated compound and 16 mg (0.03 mmol) of the title compound.

Workup

  1. stirringthe reaction mixture was stirred at room
  2. customtemperature overnight
  3. washwashed with water
  4. dry with materialThe organic layer was dried over sodium sulfate
  5. customdecanted
  6. concentrationconcentrated
  7. customPurification by flash chromatography (silica gel, hexane/ethyl acetate 2:1)

Sources & evidence

ORD record
ord-ff2043602c0a4cef8899f62f38818ded
Source dataset
uspto-grants-1995_02
Patent number
US05391566

Reaction notes

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