Pyridine → HCID 23093561, compound

HRID 2096043Notes

Reaction equation

HRID 2096043 reaction equation
OCCN(C)[C:5](=[O:11])[O:6][C:7]([CH3:10])(C)C.[CH3:13][O:14][CH2:15]C(Cl)=O.[N:19]1C=CC=C[CH:20]=1>C(OCC)(=O)C>[CH3:13][O:14][CH2:15][C:5]([O:6][CH2:7][CH2:10][NH:19][CH3:20])=[O:11]

Participants

5

Reactant 3

HCID 1049PyridineHCID 96623Methoxyacetyl chlorideHCID 545700N-(tert-Butoxycarbonyl)-N-methyl-2-aminoethanol

Product 1

HCID 23093561HCID 23093561, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

To a mixture of tert-butyl 2-hydroxyethyl(methyl)carbamate (1.75 g) obtained in Reference Synthetic Example 1 and ethyl acetate (10 mL) were added methoxyacetyl chloride (1.20 g) and pyridine (0.97 mL). After stirring at room temperature for 3 hrs, to the reaction solution was added ethyl acetate (70 mL), and washed sequentially with water (20 mL), saturated aqueous solution of sodium bicarbonate (20 mL) and water (20 mL), followed by drying over anhydrous magnesium sulfate. The solution was concentrated under reduced pressure, and the residue was dissolved in ethyl acetate (5 mL), and added 4N hydrogen chloride-ethyl acetate solution (10 mL). After stirring at room temperature for 1 hr, the solution was concentrated under reduced pressure. To the residue was added water (60 mL) and diethyl ether (30 mL), and stirred, then, the aqueous layer was separated. The aqueous layer was made basic with sodium bicarbonate, and extracted twice with ethyl acetate (40 mL). The ethyl acetate layer was dried over anhydrous magnesium sulfate, and concentrated under reduced pressure to give title compound as colorless oil (1.00 g).

Workup

  1. washwashed sequentially with water (20 mL), saturated aqueous solution of sodium bicarbonate (20 mL) and water (20 mL)
  2. dry with materialby drying over anhydrous magnesium sulfate
  3. concentrationThe solution was concentrated under reduced pressure
  4. dissolutionthe residue was dissolved in ethyl acetate (5 mL)
  5. additionadded 4N hydrogen chloride-ethyl acetate solution (10 mL)
  6. stirringAfter stirring at room temperature for 1 hr
  7. concentrationthe solution was concentrated under reduced pressure
  8. additionTo the residue was added water (60 mL) and diethyl ether (30 mL)
  9. stirringstirred
  10. customthe aqueous layer was separated
  11. extractionextracted twice with ethyl acetate (40 mL)
  12. dry with materialThe ethyl acetate layer was dried over anhydrous magnesium sulfate
  13. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-6a16170c15124966888e82634388b928
Source dataset
uspto-grants-2013_05
Patent number
US08449911B2

Reaction notes

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