Sodium hydride → 5-bromo-2-[(tert-butoxycarbonyl-ethoxycarbonylmethyl-amino)-methyl]-1-phenyl-1H-pyrrole-3-carboxylic acid ethyl ester

HRID 642213Notes

Reaction equation

HRID 642213 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[CH:10]=[C:9]([Br:11])[N:8]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:7]=1[CH2:18]Br)=[O:5])[CH3:2].[CH2:20]([O:22][C:23](=[O:33])[CH2:24][NH:25][C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[CH3:21].[H-].[Na+]>CN(C)C=O>[CH2:1]([O:3][C:4]([C:6]1[CH:10]=[C:9]([Br:11])[N:8]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:7]=1[CH2:18][N:25]([C:26]([O:28][C:29]([CH3:30])([CH3:32])[CH3:31])=[O:27])[CH2:24][C:23]([O:22][CH2:20][CH3:21])=[O:33])=[O:5])[CH3:2]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 357729Ethyl 2-((tert-butoxycarbonyl)amino)acetateHCID 684282045-bromo-2-bromomethyl-1-phenyl-1H-pyrrole-3-carboxylic acid ethyl ester

Product 1

HCID 684262925-bromo-2-[(tert-butoxycarbonyl-ethoxycarbonylmethyl-amino)-methyl]-1-phenyl-1H-pyrrole-3-carboxylic acid ethyl esterYield 85.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

5-bromo-2-bromomethyl-1-phenyl-1H-pyrrole-3-carboxylic acid ethyl ester (400 mg, 0.94 mmol) and tert-butoxycarbonylamino-acetic acid ethyl ester (182 mg, 0.897 mmol) were dissolved in dry N,N-dimethylformamide (7 mL) at 0° C. Sodium hydride (44 mg, 1.08 mmol) was then added in one portion; the mixture was stirred for 30 min at 0° C., quenched by addition of saturated ammonium chloride aqueous solution, and then extracted with ethyl acetate. The organic phase was subsequently washed with saturated sodium chloride aqueous solution, dried with anhydrous sodium sulfate, and filtered, concentrated to give an oil, which was purified by column to give the title compound (392 mg); ESI MS (m/z): 531 (M+Na+).

Workup

  1. customquenched by addition of saturated ammonium chloride aqueous solution
  2. extractionextracted with ethyl acetate
  3. washThe organic phase was subsequently washed with saturated sodium chloride aqueous solution
  4. dry with materialdried with anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto give an oil, which
  8. customwas purified by column

Sources & evidence

ORD record
ord-14b7339715a44c7cbd3ccfc938e2881b
Source dataset
uspto-grants-2010_04
Patent number
US07696223B2

Reaction notes

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