Pyridine → HCID 86606460, compound

HRID 2096046Notes

Reaction equation

HRID 2096046 reaction equation
OCCN(C)[C:5](=[O:11])[O:6][C:7]([CH3:10])(C)C.[N:13]1[CH:18]=CC=CC=1.C([Cl:29])(=O)[O:20]CC1C=CC=CC=1>CN(C)C1C=CN=CC=1.C(OCC)(=O)C>[ClH:29].[C:5](=[O:11])([OH:20])[O:6][CH2:7][CH2:10][NH:13][CH3:18]

Participants

6

Reactant 3

HCID 1049Pyridine3×HCID 10387Benzyl chloroformate3×HCID 545700N-(tert-Butoxycarbonyl)-N-methyl-2-aminoethanol

Product 1

HCID 86606460HCID 86606460, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 8857Ethyl AcetateSolvent3×

Procedure

To a mixture of tert-butyl 2-hydroxyethyl(methyl)carbamate (1.75 g) obtained in Reference Synthetic Example 1 and ethyl acetate (20 mL) were added pyridine (0.97 mL) and 4-dimethylaminopyridine (catalytic amount), and benzyl chlorocarbonate (1.57 mL) was added dropwise thereto. After stirring at room temperature for 2 hrs, pyridine (0.65 mL) and benzyl chlorocarbonate (1.28 mL) were further added. After stirring at room temperature for 5 days, pyridine (0.81 mL) was further added under ice-cooling, and a solution of benzyl chlorocarbonate (1.43 mL) in ethyl acetate (5 mL) was slowly added dropwise. The reaction solution was stirred at room temperature for 2 hrs, and added ethyl acetate (50 mL), then, washed with water (50 mL), 5% aqueous solution of citric acid (50 mL), and saturated saline (50 mL), followed by drying over anhydrous magnesium sulfate. The solution was concentrated under reduced pressure, and to the residue was added 4N hydrogen chloride-ethyl acetate solution (10 mL). After stirring at room temperature for 2 hrs, diethyl ether (10 mL) was added, and the depositting solid was collected by filtration. The solid was dried under reduced pressure to give title compound as white solid (1.99 g).

Workup

  1. additionwas added dropwise
  2. stirringAfter stirring at room temperature for 5 days
  3. temperaturecooling
  4. stirringThe reaction solution was stirred at room temperature for 2 hrs
  5. washwashed with water (50 mL), 5% aqueous solution of citric acid (50 mL), and saturated saline (50 mL)
  6. dry with materialby drying over anhydrous magnesium sulfate
  7. concentrationThe solution was concentrated under reduced pressure
  8. additionto the residue was added 4N hydrogen chloride-ethyl acetate solution (10 mL)
  9. stirringAfter stirring at room temperature for 2 hrs
  10. additiondiethyl ether (10 mL) was added
  11. filtrationthe depositting solid was collected by filtration
  12. customThe solid was dried under reduced pressure

Sources & evidence

ORD record
ord-faa5a913ee4f429495ad0282473a4f81
Source dataset
uspto-grants-2013_05
Patent number
US08449911B2

Reaction notes

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