Ethyl Acetate → (5-(Benzyloxy)-4-(2-((tert-butoxycarbonyl)amino)ethoxy)pyridin-2-yl)methyl acetate

HRID 385570Notes

Reaction equation

HRID 385570 reaction equation
[C:1]([O:4][CH2:5][C:6]1[NH:7][CH:8]=[C:9]([O:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[C:10](=[O:12])[CH:11]=1)(=[O:3])[CH3:2].Br[CH2:22][CH2:23][NH:24][C:25](=[O:31])[O:26][C:27]([CH3:30])([CH3:29])[CH3:28].C(=O)([O-])[O-].[K+].[K+].C(OCC)(=O)C>CS(C)=O.O>[C:1]([O:4][CH2:5][C:6]1[CH:11]=[C:10]([O:12][CH2:22][CH2:23][NH:24][C:25]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:31])[C:9]([O:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[CH:8][N:7]=1)(=[O:3])[CH3:2]

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 4103526tert-Butyl N-(2-bromoethyl)carbamateHCID 57815284(5-(Benzyloxy)-4-oxo-1,4-dihydropyridin-2-yl)methyl acetate

Product 1

HCID 57815373(5-(Benzyloxy)-4-(2-((tert-butoxycarbonyl)amino)ethoxy)pyridin-2-yl)methyl acetateYield 40.9%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Conditions

Temperature
85 °C

Procedure

To a solution of 6.1 g of (5-(benzyloxy)-4-oxo-1,4-dihydropyridin-2-yl)methyl acetate in 50 mL of dimethyl sulfoxide, 5.0 g of tert-butyl (2-bromoethyl)carbamate and 10 g of potassium carbonate were added, and the mixture was stirred at 80 to 90° C. for 6 hours 30 minutes. The reaction mixture was cooled to room temperature, and ethyl acetate and water were then added thereto. The organic layer was separated, washed with water and dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. The resultant residue was purified by flash silica gel column chromatography using gradient elution with chloroform:methanol=99:1 to 98:2 obtain 3.8 g of (5-(benzyloxy)-4-(2-((tert-butoxycarbonyl)amino)ethoxy)pyridin-2-yl)methyl acetate as a brown oily substance.

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. customThe organic layer was separated
  3. washwashed with water
  4. dry with materialdried over anhydrous magnesium sulfate
  5. distillationthe solvent was distilled off under reduced pressure
  6. customThe resultant residue was purified by flash silica gel column chromatography
  7. washelution with chloroform

Sources & evidence

ORD record
ord-3db56b496b48454f888f5fcda5541aa8
Source dataset
uspto-grants-2013_02
Patent number
US08367831B2

Reaction notes

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