Pyridine → HCID 23093559, compound

HRID 2096057Notes

Reaction equation

HRID 2096057 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 stirred at room temperature for 96 hrs. To the reaction solution was added ethyl acetate (500 mL), and washed with water (500 mL), aqueous solution of copper sulfate (200 mL), water (300 mL) and saturated brine (300 mL), followed by drying over anhydrous sodium sulfate. The solution was concentrated under reduced pressure to give 2-[2-[(tert-butoxycarbonyl)amino]ethoxy]ethyl ethyl carbonate as colorless oil (93.19 g).

Workup

  1. temperaturecooling
  2. washwashed with water (500 mL), aqueous solution of copper sulfate (200 mL), water (300 mL) and saturated brine (300 mL)
  3. dry with materialby drying over anhydrous sodium sulfate
  4. concentrationThe solution was concentrated under reduced pressure

Sources & evidence

ORD record
ord-3c9f26b4678c4312a604a43d12e51820
Source dataset
uspto-grants-2013_05
Patent number
US08449911B2

Reaction notes

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