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

HRID 561026
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HRID 561026 반응식
[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]
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참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 887Methanol용매
HCID 962
Water
용매

실험 절차

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+.

후처리

  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

출처 및 근거

ORD 기록
ord-df9d2dd002594aa1a5fe8f95879fe913
출처 데이터셋
uspto-grants-2011_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08063212B2

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