Pyridine → HCID 23093559, compound

HRID 874115Notes

Reaction equation

HRID 874115 reaction equation
[OH:1][CH2:2][CH2:3][O:4][CH2:5][CH2:6][NH:7][C:8](=[O:14])[O:9][C:10]([CH3:13])([CH3:12])[CH3:11].N1C=CC=CC=1.[C:21](Cl)(=[O:25])[O:22][CH2:23][CH3:24]>C(OCC)(=O)C>[C:21](=[O:25])([O:22][CH2:23][CH3:24])[O:1][CH2:2][CH2:3][O:4][CH2:5][CH2:6][NH:7][C:8]([O:9][C:10]([CH3:11])([CH3:13])[CH3:12])=[O:14]

Participants

5

Reactant 3

HCID 1049PyridineHCID 10928Ethyl chloroformateHCID 52204702-(2-Boc-aminoethoxy)ethanol

Product 1

HCID 23093559HCID 23093559, compoundYield 127.9%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

To a mixture of tert-butyl [2-(2-hydroxyethoxy)ethyl]carbamate (53.93 g) obtained above and ethyl acetate (350 mL) were added pyridine (53.78 mL) and ethyl chlorocarbonate (70.57 g) under ice-cooling, and the mixture was stirred at room temperature for 96 hrs. Ethyl acetate (500 mL) was added to the reaction mixture, and the mixture was washed with water (500 mL), an aqueous copper sulfate solution (200 mL), water (300 mL) and saturated brine (300 mL) and dried over anhydrous sodium sulfate. Concentration under reduced pressure gave 2-[2-[(tert-butoxycarbonyl)amino]ethoxy]ethyl ethyl carbonate (93.19 g) as a colorless oil.

Workup

  1. temperaturecooling
  2. washthe mixture was washed with water (500 mL)
  3. dry with materialan aqueous copper sulfate solution (200 mL), water (300 mL) and saturated brine (300 mL) and dried over anhydrous sodium sulfate
  4. concentrationConcentration under reduced pressure

Sources & evidence

ORD record
ord-1d4d10e89f7a488fa54ab2897585cae1
Source dataset
uspto-grants-2015_03
Patent number
US08980322B2

Reaction notes

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