Water → HCID 21846511, compound

HRID 1274169Notes

Reaction equation

HRID 1274169 reaction equation
C(=O)([O-])[O-].[K+].[K+].[CH2:7](Br)[CH3:8].[N:10]1[CH:15]=[CH:14][C:13]([NH:16][C:17](=[O:34])[C:18]2[CH:23]=[CH:22][C:21]([CH2:24][NH:25][C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])=[CH:20][C:19]=2[OH:33])=[CH:12][CH:11]=1.O>CN(C)C=O>[N:10]1[CH:15]=[CH:14][C:13]([NH:16][C:17](=[O:34])[C:18]2[CH:23]=[CH:22][C:21]([CH2:24][NH:25][C:26]([O:28][C:29]([CH3:30])([CH3:31])[CH3:32])=[O:27])=[CH:20][C:19]=2[O:33][CH2:7][CH3:8])=[CH:12][CH:11]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6332Ethyl BromideHCID 11430Potassium CarbonateHCID 22120656HCID 22120656, compound

Product 1

HCID 21846511HCID 21846511, compoundYield 55.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Potassium carbonate (40 mg) and ethyl bromide (56 mg) were added to a solution of N-(4- pyridyl)-4-tert-butoxycarbonylaminomethyl-2-hydroxybenzamide (100 mg) in dimethylformamide (10 ml), and the mixture was stirred at room temperature for 4 hours. After the reaction, water was added, and the mixture was extracted with ethyl acetate. The extract was washed with water, dried, and concentrated under reduced pressure. The obtained crystals were recrystallized form ethyl acetate-hexane to give 60 mg of N-(4- pyridyl)-4-tert-butoxycarbonylaminomethyl-2-ethoxybenzamide.

Workup

  1. additionwas added
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe extract was washed with water
  4. customdried
  5. concentrationconcentrated under reduced pressure
  6. customThe obtained crystals were recrystallized
  7. customform ethyl acetate-hexane

Sources & evidence

ORD record
ord-66bcb93fe7714f22861987c0ecfd25f8
Source dataset
uspto-grants-2000_12
Patent number
US06156766

Reaction notes

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