Ethyl bromoacetate → HCID 22100695, compound

HRID 1458412Notes

Reaction equation

HRID 1458412 reaction equation
[CH3:1][C:2]1[N:6]([CH2:7][C:8]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[C:11]([C:18]#[N:19])=[CH:10][CH:9]=2)[C:5]2[CH:20]=[C:21]([O:25][CH:26]3[CH2:31][CH2:30][N:29]([C:32]([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33])[CH2:28][CH2:27]3)[C:22]([OH:24])=[CH:23][C:4]=2[N:3]=1.[H-].[Na+].Br[CH2:42][C:43]([O:45][CH2:46][CH3:47])=[O:44].C(OCC)(=O)C>CN(C=O)C.O>[CH3:1][C:2]1[N:6]([CH2:7][C:8]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[C:11]([C:18]#[N:19])=[CH:10][CH:9]=2)[C:5]2[CH:20]=[C:21]([O:25][CH:26]3[CH2:31][CH2:30][N:29]([C:32]([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33])[CH2:28][CH2:27]3)[C:22]([O:24][CH2:42][C:43]([O:45][CH2:46][CH3:47])=[O:44])=[CH:23][C:4]=2[N:3]=1

Participants

7

Reactant 4

HCID 7748Ethyl bromoacetateHCID 8857Ethyl AcetateHCID 24758Sodium hydrideHCID 22100737HCID 22100737, compound

Product 1

HCID 22100695HCID 22100695, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To 2-methyl-5-hydroxy-6-(N-(tert-butoxycarbonyl)piperidin-4-yloxy)-1-(4-cyanonaphth-1-yl)methylbenzimidazole (1.11 g) in DMF (50 mL) was added NaH (0.15 g) at ambient temperature. After stirring at ambient for 30 minutes ethyl bromoacetate (0.4 mL) was added. The reaction was stirred at ambient temperature for 1 hour and was worked up between ethyl acetate and H2O. The organic layer was dried, concentrated and purified by silica gel chromatography (hexane/ethyl acetate/CH2Cl2 /methanol, gradient) to afford 2-methyl-5-(ethoxycarbonylmethoxy)-6-(N-(tert-butoxycarbonyl)piperidin-4-yloxy)-1-(4-cyanonaphth-1-yl)methylbenzimidazole.

Workup

  1. additionwas added
  2. customThe organic layer was dried
  3. concentrationconcentrated
  4. custompurified by silica gel chromatography (hexane/ethyl acetate/CH2Cl2 /methanol, gradient)

Sources & evidence

ORD record
ord-ebe717e578194262a24b98995e2afe7b
Source dataset
uspto-grants-1998_12
Patent number
US05849759

Reaction notes

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