Trifluoroacetic acid → HCID 15287674, compound

HRID 275409Notes

Reaction equation

HRID 275409 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 0.25N 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 0.25N 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-408f479833594b56aeb3327f19e01ffd
Source dataset
uspto-grants-1995_02
Patent number
US05393764

Reaction notes

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