Potassium Carbonate → Benzyl 2-(2-(methylcarbamoyl)morpholino)acetate

HRID 889215Notes

Reaction equation

HRID 889215 reaction equation
[CH3:1][NH:2][C:3]([CH:5]1[O:10][CH2:9][CH2:8][N:7]([C:11](OC(C)(C)C)=O)[CH2:6]1)=[O:4].C([O-])([O-])=O.[K+].[K+].[CH2:24]([O:31][C:32](=[O:35])CBr)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>C(Cl)Cl.C(O)(C(F)(F)F)=O.C(OCC)(=O)C.O>[CH3:1][NH:2][C:3]([CH:5]1[CH2:6][N:7]([CH2:11][C:32]([O:31][CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)=[O:35])[CH2:8][CH2:9][O:10]1)=[O:4]

Participants

8

Reactant 3

HCID 11430Potassium CarbonateHCID 62576Benzyl bromoacetateHCID 66760938Tert-butyl 2-(methylcarbamoyl)morpholine-4-carboxylate

Product 1

HCID 66760795Benzyl 2-(2-(methylcarbamoyl)morpholino)acetate

Reagents, catalysts & solvents 4

HCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolventHCID 8857Ethyl AcetateSolvent

Procedure

tert-butyl 2-(methylcarbamoyl)morpholine-4-carboxylate prepared above (0.5 g, 0.20 mmol) was dissolved in DCM (10 mL) and TFA (2 mL). The reaction mixture was stirred at room temperature for 4 h and then concentrated; excess 1N HCl solution in ether was added to the residue and concentrated under high vacuum. The residue was dissolved in acetonitrile (20 mL) and K2CO3 (0.56 g, 40.8 mmol) was added followed by bromo-acetic acid benzyl ester (0.7 g, 3.07 mmol). The reaction mixture was heated at 60° C. overnight. The solution was cooled to room temperature and diluted with Ethyl acetate (50 mL) and water (50 mL), organic layer was separated, dried (MgSO4) and concentrated to give an oil which was purified by column chromatography using ethyl acetate-hexanes (1:1) to give benzyl 2-(2-(methylcarbamoyl)morpholino)acetate. MS (APCI) 293 (M+).

Workup

  1. concentrationconcentrated
  2. additionexcess 1N HCl solution in ether was added to the residue
  3. concentrationconcentrated under high vacuum
  4. dissolutionThe residue was dissolved in acetonitrile (20 mL)
  5. temperatureThe reaction mixture was heated at 60° C. overnight
  6. temperatureThe solution was cooled to room temperature
  7. customwas separated
  8. dry with materialdried (MgSO4)
  9. concentrationconcentrated
  10. customto give an oil which
  11. customwas purified by column chromatography

Sources & evidence

ORD record
ord-f0ce767ba1e9435bbb4f8676414f6827
Source dataset
uspto-grants-2012_08
Patent number
US08252793B2

Reaction notes

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