Sodium hydride → HCID 68428329, compound

HRID 642404Notes

Reaction equation

HRID 642404 reaction equation
[CH2:1]([O:3][C:4](=[O:14])[CH2:5][NH:6][C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[CH3:2].[H-].[Na+].[CH2:17]([O:19][C:20]([C:22]1[C:26]([Cl:27])=[C:25]([Cl:28])[N:24]([CH2:29][CH2:30][CH:31]([CH3:33])[CH3:32])[C:23]=1[CH2:34]Br)=[O:21])[CH3:18]>CN(C=O)C>[CH2:17]([O:19][C:20]([C:22]1[C:26]([Cl:27])=[C:25]([Cl:28])[N:24]([CH2:29][CH2:30][CH:31]([CH3:33])[CH3:32])[C:23]=1[CH2:34][N:6]([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[CH2:5][C:4]([O:3][CH2:1][CH3:2])=[O:14])=[O:21])[CH3:18]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 357729Ethyl 2-((tert-butoxycarbonyl)amino)acetateHCID 68428407HCID 68428407, compound

Product 1

HCID 68428329HCID 68428329, compoundYield 99.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a solution of tert-butoxycarbonylamino-acetic acid ethyl ester (10.4 g, 51.3 mmol) in 90 mL of N,N′-dimethylformamide at 0° C. was added sodium hydride (60% dispersion in mineral oil, 2.35 g, 58.7 mmol). The ice bath was then removed, and the reaction mixture was stirred at ambient temperature for 10 min. After the reaction mixture was cooled at 0° C., the crude 4,5-dichloro-2-bromomethyl-1-(3-methyl-butyl)-1H-pyrrole-3-carboxylic acid ethyl ester (18.1 g, 48.9 mmol) in 20 mL of N,N′-dimethylformamide was added. The ice bath was removed, and the reaction mixture was stirred at ambient temperature for 1 hour. Saturated ammonium chloride aqueous solution (200 mL) and ethyl acetate (350 mL) were added to quench the reaction. The organic layer was washed with water and saturated sodium chloride aqueous solution, dried, filtered, and concentrated to afford 24.1 g of the crude 2-[(tert-butoxycarbonyl-ethoxycarbonylmethyl-amino)-methyl]-4,5-dichloro-1-(3-methyl-butyl)-1H-pyrrole-3-carboxylic acid ethyl ester as a black oil.

Workup

  1. customThe ice bath was then removed
  2. temperatureAfter the reaction mixture was cooled at 0° C.
  3. customThe ice bath was removed
  4. stirringthe reaction mixture was stirred at ambient temperature for 1 hour
  5. additionSaturated ammonium chloride aqueous solution (200 mL) and ethyl acetate (350 mL) were added
  6. customto quench
  7. customthe reaction
  8. washThe organic layer was washed with water and saturated sodium chloride aqueous solution
  9. customdried
  10. filtrationfiltered
  11. concentrationconcentrated

Sources & evidence

ORD record
ord-13b9bb9e9ddd40788115af8442465232
Source dataset
uspto-grants-2010_04
Patent number
US07696223B2

Reaction notes

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