Water → Benzyl {3-[({5-[(tert-butoxycarbonyl)(methyl)amino]pyridin-2-yl}carbonyl)(methyl)amino]propyl}methylcarbamate

HRID 446508Notes

Reaction equation

HRID 446508 reaction equation
[C:1]([O:5][C:6]([NH:8][C:9]1[CH:10]=[CH:11][C:12]([C:15]([N:17]([CH3:33])[CH2:18][CH2:19][CH2:20][N:21]([CH3:32])[C:22](=[O:31])[O:23][CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)=[O:16])=[N:13][CH:14]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].[CH3:36]I.O>O1CCCC1>[C:1]([O:5][C:6]([N:8]([CH3:36])[C:9]1[CH:10]=[CH:11][C:12]([C:15]([N:17]([CH3:33])[CH2:18][CH2:19][CH2:20][N:21]([CH3:32])[C:22](=[O:31])[O:23][CH2:24][C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=2)=[O:16])=[N:13][CH:14]=1)=[O:7])([CH3:2])([CH3:4])[CH3:3]

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 66671652Benzyl {3-[({5-[(tert-butoxycarbonyl)amino]pyridin-2-yl}carbonyl)(methyl)amino]propyl}methylcarbamate

Product 1

HCID 66671837Benzyl {3-[({5-[(tert-butoxycarbonyl)(methyl)amino]pyridin-2-yl}carbonyl)(methyl)amino]propyl}methylcarbamateYield 101.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The compound (170 mg, 0.372 mmol) obtained in Example 6a was dissolved in tetrahydrofuran (4 mL), sodium hydride (55%; 20 mg, 0.447 mmol) was added under ice cooling, and the mixture was stirred at room temperature for 15 minutes. Methyl iodide (35 μL, 0.558 mmol) was added, and then the mixture was stirred overnight at room temperature. Water was added to the reaction mixture, the mixture was extracted with ethyl acetate (×3), and the organic layer was washed with saturated sodium chloride solution. The organic layer was dried with anhydrous sodium sulfate, and then the solvent was evaporated under reduced pressure to give the title compound (178 mg; yield, 100%) as a yellow oily substance.

Workup

  1. stirringthe mixture was stirred overnight at room temperature
  2. extractionthe mixture was extracted with ethyl acetate (×3)
  3. washthe organic layer was washed with saturated sodium chloride solution
  4. dry with materialThe organic layer was dried with anhydrous sodium sulfate
  5. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-1349fb63ca19458da5fe248de8e3efea
Source dataset
uspto-grants-2013_07
Patent number
US08476253B2

Reaction notes

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