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

HRID 539620Notes

Reaction equation

HRID 539620 reaction equation
[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

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-b013e59eb7fe4c13be2b74af56e49030
Source dataset
uspto-grants-2014_10
Patent number
US08871760B2

Reaction notes

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