Trifluoroacetic acid → HCID 15287674, compound

HRID 1885936Notes

Reaction equation

HRID 1885936 reaction equation
[CH3:1][C:2]([C:5]1[CH:10]=[C:9]([S:11][C@@H:12]2[CH2:17][CH2:16][CH2:15][CH2:14][C@H:13]2O)[CH:8]=[C:7]([C:19]([CH3:22])([CH3:21])[CH3:20])[C:6]=1[OH:23])([CH3:4])[CH3:3].FC(F)(F)C(O)=O.[C:31]([O:35][CH3:36])(=[O:34])[CH2:32][SH:33]>>[CH3:3][C:2]([C:5]1[CH:10]=[C:9]([S:11][C@@H:12]2[CH2:17][CH2:16][CH2:15][CH2:14][C@H:13]2[S:33][CH2:32][C:31]([O:35][CH3:36])=[O:34])[CH:8]=[C:7]([C:19]([CH3:22])([CH3:20])[CH3:21])[C:6]=1[OH:23])([CH3:1])[CH3:4]

Participants

4

Reactant 3

HCID 6422Trifluoroacetic acidHCID 16907Methyl ThioglycolateHCID 15287673HCID 15287673, compound

Product 1

HCID 15287674HCID 15287674, compound

Procedure

The compound of Example 15 (2.0 g, 0.0059) was added to trifluoroacetic acid (5 ml). After several minutes methyl thioglycolate (0.63 g) was added, and the reaction mixture was stirred at room temperature for 2 hours. The trifluoroacetic acid was evaporated with a gentle flow of nitrogen gas. The residue was dissolved in diethyl ether (50 ml) and washed twice with 2 ml of 0.25 N NaOH, dried over anhydrous magnesium sulfate, filtered and concentrated to an oil. The product was purified by silica gel chromatography to give a colorless oil. The structure was supported by NMR, infrared and elemental analysis.

Workup

  1. customThe trifluoroacetic acid was evaporated with a gentle flow of nitrogen gas
  2. dissolutionThe residue was dissolved in diethyl ether (50 ml)
  3. washwashed twice with 2 ml of 0.25 N NaOH
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated to an oil
  7. customThe product was purified by silica gel chromatography
  8. customto give a colorless oil

Sources & evidence

ORD record
ord-0b2702cb2a3740fb8e71d86af7fb2aa7
Source dataset
uspto-grants-1992_09
Patent number
US05147893

Reaction notes

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