Trifluoroacetic acid → HCID 10063674, compound

HRID 1975190Notes

Reaction equation

HRID 1975190 reaction equation
C(O[CH:4](OCC)[CH2:5][NH:6][C:7](=[CH:16][S:17]([C:20]([F:23])([F:22])[F:21])(=[O:19])=[O:18])[C:8]1[CH:13]=[CH:12][C:11]([O:14][CH3:15])=[CH:10][CH:9]=1)C.FC(F)(F)C(O)=O>C(OCC)(=O)C.CCCCCCC>[CH3:15][O:14][C:11]1[CH:12]=[CH:13][C:8]([C:7]2[NH:6][CH:5]=[CH:4][C:16]=2[S:17]([C:20]([F:23])([F:22])[F:21])(=[O:19])=[O:18])=[CH:9][CH:10]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 67655879HCID 67655879, compound

Product 1

HCID 10063674HCID 10063674, compound

Reagents, catalysts & solvents 1

HCID 21899848Ethylacetate heptaneSolvent

Procedure

The oil obtained in Example 3 is treated with trifluoroacetic acid (20 mL), stirred for several hours at room temperature, concentrated in vacuo and chased with ethyl acetate to obtain an oil. Flash chromatography of the oil using silica gel and a 1:4 ethyl acetate/heptane solution gives a yellow semi-solid. Recrystallization of the semi-solid gives the title product as a yellow solid (0.88 g, mp 138.5°-140.5° C.) which is identified by 1HNMR and 13CNMR spectral analyses.

Workup

  1. concentrationconcentrated in vacuo and chased with ethyl acetate
  2. customto obtain an oil
  3. customRecrystallization of the semi-solid

Sources & evidence

ORD record
ord-b815b75c942c4c9a82ad1f9afa11f3c9
Source dataset
uspto-grants-1994_02
Patent number
US05284863

Reaction notes

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