Hydrochloric Acid → [2-(2-Oxo-2,3-dihydro-imidazol-1-yl)-ethyl]-carbamic acid tert-butyl ester

HRID 561026Notes

Reaction equation

HRID 561026 reaction equation
[C:1]([O:5][C:6](=[O:22])[NH:7][CH2:8][CH2:9][NH:10][C:11]([NH:13][CH2:14][CH:15](OCC)OCC)=[O:12])([CH3:4])([CH3:3])[CH3:2].Cl.[OH-].[K+]>CO.O>[C:1]([O:5][C:6](=[O:22])[NH:7][CH2:8][CH2:9][N:10]1[CH:15]=[CH:14][NH:13][C:11]1=[O:12])([CH3:2])([CH3:3])[CH3:4]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 86640494{2-[3-(2,2-Diethoxy-ethyl)-ureido]-ethyl}-carbamic acid tert-butyl ester

Product 1

HCID 66997754[2-(2-Oxo-2,3-dihydro-imidazol-1-yl)-ethyl]-carbamic acid tert-butyl esterYield 54.7%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

Dissolve {2-[3-(2,2-diethoxy-ethyl)-ureido]-ethyl}-carbamic acid tert-butyl ester (6.5 g, 20.35 mmol) in methanol (75 mL) and water (40 mL). To the reaction mixture add HCl (0.4 N, 50 mL) dropwise over 30 min. Stir the mixture overnight and neutralize by adding KOH (0.4 M, 50 mL), and concentrate in vacuo. Extract the residue in chloroform and wash with saturated aqueous sodium chloride, dry over MgSO4, filter and remove solvent on a rotovap to give a crude white solid. Purify by column chromatography 1% to 10% MeOH in dichloromethane to afford the pure product as a white solid (2.53 g, 11.13 mmol). GCMS (EI) m/z 227 M+.

Workup

  1. concentrationconcentrate in vacuo
  2. extractionExtract the residue in chloroform
  3. washwash with saturated aqueous sodium chloride
  4. dry with materialdry over MgSO4
  5. filtrationfilter
  6. customremove solvent on a rotovap
  7. customto give a crude white solid
  8. customPurify by column chromatography 1% to 10% MeOH in dichloromethane

Sources & evidence

ORD record
ord-df9d2dd002594aa1a5fe8f95879fe913
Source dataset
uspto-grants-2011_11
Patent number
US08063212B2

Reaction notes

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