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Potassium Carbonate → [2-tert-Butoxycarbonylamino-2-(4-fluoro-phenyl)-ethylsulfanyl]-acetic acid methyl ester

HRID 539620
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HRID 539620 반응식
[C:1]([O:5][C:6](=[O:18])[NH:7][CH:8]([C:11]1[CH:16]=[CH:15][C:14]([F:17])=[CH:13][CH:12]=1)[CH2:9]I)([CH3:4])([CH3:3])[CH3:2].[CH3:19][O:20][C:21](=[O:24])[CH2:22][SH:23].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[CH3:19][O:20][C:21](=[O:24])[CH2:22][S:23][CH2:9][CH:8]([NH:7][C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:18])[C:11]1[CH:16]=[CH:15][C:14]([F:17])=[CH:13][CH:12]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 3

HCID 11430Potassium CarbonateHCID 16907Methyl ThioglycolateHCID 58200314[1-(4-Fluoro-phenyl)-2-iodo-ethyl]-carbamic acid tert-butyl ester

생성물 1

HCID 58200302[2-tert-Butoxycarbonylamino-2-(4-fluoro-phenyl)-ethylsulfanyl]-acetic acid methyl ester수율 91.8%

시약·촉매·용매 1

HCID 180Acetone용매

실험 절차

A mixture of [1-(4-fluoro-phenyl)-2-iodo-ethyl]-carbamic acid tert-butyl ester (3.88 g, 10.6 mmol), mercapto-acetic acid methyl ester (1.24 g, 11.7 mmol) and potassium carbonate (12.21 g, 18 mmol) in acetone (100 mL) was heated to reflux with stirring for 90 minutes. The mixture was then cooled and concentrated under reduced pressure. The residue was partitioned between water and ethyl acetate, and the organic layer was separated, washed with brine, dried (MgSO4), filtered and concentrated under reduced pressure. The residue was recrystallized from hexanes to give 3.34 g of [2-tert-Butoxycarbonylamino-2-(4-fluoro-phenyl)-ethylsulfanyl]-acetic acid methyl ester, MP=61-62° C.

후처리

  1. temperaturewas heated
  2. temperatureto reflux
  3. temperatureThe mixture was then cooled
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was partitioned between water and ethyl acetate
  6. customthe organic layer was separated
  7. washwashed with brine
  8. dry with materialdried (MgSO4)
  9. filtrationfiltered
  10. concentrationconcentrated under reduced pressure
  11. customThe residue was recrystallized from hexanes

출처 및 근거

ORD 기록
ord-b013e59eb7fe4c13be2b74af56e49030
출처 데이터셋
uspto-grants-2014_10
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08871760B2

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