Sodium hydride → 2-tert-Butoxycarbonylamino-3-(4-fluoro-phenylsulfanyl)-propionic Acid Methyl Ester

HRID 987937Notes

Reaction equation

HRID 987937 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([SH:8])=[CH:4][CH:3]=1.[H-].[Na+].[CH3:11][O:12][C:13](=[O:35])[CH:14]([NH:27][C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])[CH2:15]OS(C1C=CC(C)=CC=1)(=O)=O>CN(C)C=O>[CH3:11][O:12][C:13](=[O:35])[CH:14]([NH:27][C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])[CH2:15][S:8][C:5]1[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 677894-FluorothiophenolHCID 28181622-Tert-butoxycarbonylamino-3-(toluene-4-sulfonyloxy)-propionic acid methyl ester

Product 1

HCID 698535532-tert-Butoxycarbonylamino-3-(4-fluoro-phenylsulfanyl)-propionic Acid Methyl Ester

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A stirred solution of 4-fluorothiophenol (1.24 g, 9.65 mmol) in N,N-dimethyl formamide (10 ml) was treated with sodium hydride (240 mg, 9.37 mmol) and the reaction mixture was stirred at room temperature for 30 minutes. 2-tert-Butoxycarbonylamino-3-(toluene-4-sulfonyloxy)-propionic acid methyl ester (3 g, 8.04 mmol) in N,N dimethyl formamide (ml) was added, the resulting mixture was stirred for two hours and then concentrated in vacuo. The residue was dissolved in ethyl acetate (100 ml) and washed with water (2*80 ml) and brine. The organic layer was dried (anhydrous magnesium sulfate) and concentrated in vacuo to give, after purification by flash chromatography on silica gel, 2-tert-butoxycarbonylamino-3-(4-fluoro-phenylsulfanyl)-propionic acid methyl ester (2.28 g, 83%) as a yellow oil.

Workup

  1. stirringthe resulting mixture was stirred for two hours
  2. concentrationconcentrated in vacuo
  3. dissolutionThe residue was dissolved in ethyl acetate (100 ml)
  4. washwashed with water (2*80 ml) and brine
  5. dry with materialThe organic layer was dried (anhydrous magnesium sulfate)
  6. concentrationconcentrated in vacuo
  7. customto give
  8. customafter purification by flash chromatography on silica gel, 2-tert-butoxycarbonylamino-3-(4-fluoro-phenylsulfanyl)-propionic acid methyl ester (2.28 g, 83%) as a yellow oil

Sources & evidence

ORD record
ord-b64c81fbdb9f4444baef37d83817bdde
Source dataset
uspto-grants-2003_10
Patent number
US06632826B1

Reaction notes

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