Tetrabutylammonium Fluoride → HCID 18394989, compound

HRID 1602964Notes

Reaction equation

HRID 1602964 reaction equation
[C:1]1([CH:7]([C:46]2[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=2)[C:8]2[C:9](=[S:45])[NH:10][C:11](=[O:44])[N:12]([CH:43]=2)[C@@H:13]2[O:42][C@H:32]([CH2:33][O:34][Si](C(C)(C)C)(C)C)[C@@H:23]([O:24][Si](C(C)(C)C)(C)C)[C@H:14]2[O:15][Si](C(C)(C)C)(C)C)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1>[C:46]1([CH:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[C:8]2[C:9](=[S:45])[NH:10][C:11](=[O:44])[N:12]([CH:43]=2)[C@@H:13]2[O:42][C@H:32]([CH2:33][OH:34])[C@@H:23]([OH:24])[C@H:14]2[OH:15])[CH:47]=[CH:48][CH:49]=[CH:50][CH:51]=1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 18394987HCID 18394987, compound

Product 1

HCID 18394989HCID 18394989, compoundYield 42.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The product of step (ii) (5.5 g) was treated with 1M tetra-n-butylammonium fluoride in tetrahydrofuran (21.5 ml) at room temperature. After stirring for 2 hours the solvent was removed under reduced pressure and the residue was purified by flash silica-gel chromatography eluting with ethyl acetate/iso-hexane mixtures to afford 5-diphenylmethyl-4-thiouridine as a yellow solid (1.3 g).

Workup

  1. customwas removed under reduced pressure
  2. customthe residue was purified by flash silica-gel chromatography
  3. washeluting with ethyl acetate/iso-hexane

Sources & evidence

ORD record
ord-55ee20b53b10430f8e63a76a5cfcf610
Source dataset
uspto-grants-1999_11
Patent number
US05985849

Reaction notes

Loading…