Trifluoroacetic acid → HCID 87064139, compound

HRID 1091304Notes

Reaction equation

HRID 1091304 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:22][C@@H:17]2[C@H:18]([O:19][CH2:20][CH3:21])[C@H:12]1[CH:13]([O:16]2)[O:14]C)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.FC(F)(F)C(O)=O>>[CH2:1]([O:8][C:9]([N:11]1[CH2:22][C@@H:17]([OH:16])[C@H:18]([O:19][CH2:20][CH3:21])[C@H:12]1[CH:13]=[O:14])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acidHCID 66591955HCID 66591955, compound

Product 1

HCID 87064139HCID 87064139, compoundYield 77%

Procedure

To an aqueous solution (1 mL) of methyl N-benzyloxycarbonyl-2,5-dideoxy-3-O-ethyl-2,5-imino-D-lyxofuranoside, trifluoroacetic acid (1 mL) was added, and the mixture was stirred for three hours. The reaction liquor was concentrated under reduced pressure, and the obtained residue was extracted with methylene chloride. The extract was washed with saturated brine, and dried over anhydrous sodium sulfate. The solvent was concentrated under reduced pressure, and the obtained residue was purified by thin layer chromatography (ethyl acetate:n-hexane=1:1, v/v), to obtain the title compound (92 mg, 77%) as an oily matter.

Workup

  1. concentrationThe reaction liquor was concentrated under reduced pressure
  2. extractionthe obtained residue was extracted with methylene chloride
  3. washThe extract was washed with saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationThe solvent was concentrated under reduced pressure
  6. customthe obtained residue was purified by thin layer chromatography (ethyl acetate

Sources & evidence

ORD record
ord-d5c7517da7614fc0acfb8db975970eae
Source dataset
uspto-grants-2012_03
Patent number
US08129366B2

Reaction notes

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