Trifluoroacetic acid → HCID 54540070, compound

HRID 1602969Notes

Reaction equation

HRID 1602969 reaction equation
O[C:2]1([C:15]2[C:16](=[O:31])[NH:17][C:18](=[O:30])[N:19]([CH:29]=2)[C@@H:20]2[O:28][C@H:25]([CH2:26][OH:27])[C@@H:23]([OH:24])[C@H:21]2[OH:22])[C:14]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[C:8]2[C:3]1=[CH:4][CH:5]=[CH:6][CH:7]=2.C([SiH](CC)CC)C.FC(F)(F)C(O)=O>ClCCl>[CH:13]1[C:14]2[CH:2]([C:15]3[C:16](=[O:31])[NH:17][C:18](=[O:30])[N:19]([CH:29]=3)[C@@H:20]3[O:28][C@H:25]([CH2:26][OH:27])[C@@H:23]([OH:24])[C@H:21]3[OH:22])[C:3]3[C:8](=[CH:7][CH:6]=[CH:5][CH:4]=3)[C:9]=2[CH:10]=[CH:11][CH:12]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 53965118HCID 53965118, compound

Product 1

HCID 54540070HCID 54540070, compoundYield 33.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The product of step (ii) (3.37 g) was dissolved in dichloromethane (100 ml) and triethylsilane (1.39 ml) and treated with trifluoroacetic acid (6.23 ml). The mixture was stirred at room temperature for 36 hours. The solvent was evaporated under reduced pressure and the residue azeotroped three times with toluene. The remaining residue was purified by flash chromatography on silica-gel eluting with 15% methanol in ethyl acetate to give 5-(9H-fluoren-9-yl)uridine as white powder (1.09 g).

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. customthe residue azeotroped three times with toluene
  3. customThe remaining residue was purified by flash chromatography on silica-gel
  4. washeluting with 15% methanol in ethyl acetate

Sources & evidence

ORD record
ord-c0896ef4586943929ac902903a61a319
Source dataset
uspto-grants-1999_11
Patent number
US05985849

Reaction notes

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