Trifluoroacetic acid → HCID 10873283, compound

HRID 1602953Notes

Reaction equation

HRID 1602953 reaction equation
O[C:2]([C:15]1[C:16](=[O:52])[NH:17][C:18](=[O:51])[N:19]([CH:50]=1)[C@@H:20]1[O:49][C@H:39]([CH2:40][O:41][Si](C(C)(C)C)(C)C)[C@@H:30]([O:31][Si](C(C)(C)C)(C)C)[C@H:21]1[O:22][Si](C(C)(C)C)(C)C)([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.FC(F)(F)C(O)=O>ClCCl.C([SiH](CC)CC)C>[C:9]1([CH:2]([C:3]2[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=2)[C:15]2[C:16](=[O:52])[NH:17][C:18](=[O:51])[N:19]([CH:50]=2)[C@@H:20]2[O:49][C@H:39]([CH2:40][OH:41])[C@@H:30]([OH:31])[C@H:21]2[OH:22])[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acidHCID 18394995HCID 18394995, compound

Product 1

HCID 10873283HCID 10873283, compoundYield 84.2%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 12052TriethylsilaneSolvent

Procedure

The product of step (i) (8.9 g) was dissolved in dichloromethane (100 ml) and triethylsilane (2 ml). Trifluoroacetic acid (8.9 ml) was added dropwise over 5 minutes and the mixture was stirred for a further 20 minutes. The volatiles were removed under reduced pressure and any residual traces were removed by addition of toluene (50 ml) and evaporation under reduced pressure (three times). The residual gum was treated with tetra-n-butylammonium fluoride (35 ml of a 1M solution in tetrahydrofuran) for 1 hour at room temperature. The volatiles were removed under reduced pressure and the gummy residue purified by silica-gel chromatography eluting with chloroform-methanol mixtures to give 5-diphenylmethyluridine as a white solid (4 g).

Workup

  1. customThe volatiles were removed under reduced pressure
  2. customany residual traces were removed by addition of toluene (50 ml) and evaporation under reduced pressure (three times)
  3. additionThe residual gum was treated with tetra-n-butylammonium fluoride (35 ml of a 1M solution in tetrahydrofuran) for 1 hour at room temperature
  4. customThe volatiles were removed under reduced pressure
  5. customthe gummy residue purified by silica-gel chromatography
  6. washeluting with chloroform-methanol mixtures

Sources & evidence

ORD record
ord-f60d9afd2bea4c9e94dbe25c4666a505
Source dataset
uspto-grants-1999_11
Patent number
US05985849

Reaction notes

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