Trifluoroacetic acid → HCID 54298480, compound

HRID 1602966Notes

Reaction equation

HRID 1602966 reaction equation
O[C:2]([C:19]1[C:20](=[O:56])[NH:21][C:22](=[O:55])[N:23]([CH:54]=1)[C@@H:24]1[O:53][C@H:43]([CH2:44][O:45][Si](C(C)(C)C)(C)C)[C@@H:34]([O:35][Si](C(C)(C)C)(C)C)[C@H:25]1[O:26][Si](C(C)(C)C)(C)C)([C:11]1[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][CH:12]=1)[C:3]1[CH:8]=[CH:7][C:6]([O:9][CH3:10])=[CH:5][CH:4]=1.C([SiH](CC)CC)C.FC(F)(F)C(O)=O>ClCCl>[CH3:10][O:9][C:6]1[CH:7]=[CH:8][C:3]([CH:2]([C:19]2[C:20](=[O:56])[NH:21][C:22](=[O:55])[N:23]([CH:54]=2)[C@@H:24]2[O:53][C@H:43]([CH2:44][OH:45])[C@@H:34]([OH:35])[C@H:25]2[OH:26])[C:11]2[CH:12]=[CH:13][C:14]([O:17][CH3:18])=[CH:15][CH:16]=2)=[CH:4][CH:5]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 18394994HCID 18394994, compound

Product 1

HCID 54298480HCID 54298480, compoundYield 64.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The product of step (i) (3.8 g) was dissolved in dichloromethane (75 ml) and triethylsilane (0.8 ml) and was treated with trifluoroacetic acid(3.59 ml). After stirring for 1 hour at room temperature, the volatiles were removed under reduced pressure and any remaining traces removed by azeotroping four times with toluene. The residue was treated with 1M tetra-n-butylammonium fluoride solution in tetrahydrofuran (15 ml). After stirring for 36 hours, the solvent was removed under reduced pressure and the residue was purified by silica-gel chromatography eluting with 2% methanol in ethyl acetate to afford 5-(1,1-bis(4-methoxyphenyl)methyl)uridine as a white solid (1.4 g).

Workup

  1. customthe volatiles were removed under reduced pressure
  2. customany remaining traces removed
  3. customby azeotroping four times with toluene
  4. additionThe residue was treated with 1M tetra-n-butylammonium fluoride solution in tetrahydrofuran (15 ml)
  5. stirringAfter stirring for 36 hours
  6. customthe solvent was removed under reduced pressure
  7. customthe residue was purified by silica-gel chromatography
  8. washeluting with 2% methanol in ethyl acetate

Sources & evidence

ORD record
ord-0988342b4e7248348f37af4490778d64
Source dataset
uspto-grants-1999_11
Patent number
US05985849

Reaction notes

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