Trifluoroacetic acid → HCID 54112621, compound

HRID 1508617Notes

Reaction equation

HRID 1508617 reaction equation
FC(F)(F)C(O)=O.[F:8][C@H:9]1[C@H:13]([O:14]CC2C=CC(OC)=CC=2)[C@@H:12]([CH2:24][O:25]CC2C=CC(OC)=CC=2)[S:11][CH:10]1[N:35]1[CH:42]=[CH:41][C:39]([NH2:40])=[N:38][C:36]1=[O:37]>ClCCl>[F:8][C@H:9]1[C@H:13]([OH:14])[C@@H:12]([CH2:24][OH:25])[S:11][CH:10]1[N:35]1[CH:42]=[CH:41][C:39]([NH2:40])=[N:38][C:36]1=[O:37]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 89975723HCID 89975723, compound

Product 1

HCID 54112621HCID 54112621, compoundYield 67.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

0.2 mL of trifluoroacetic acid was added to a solution of 8.8 mg of 1-(2-deoxy-2-fluoro-3,5-bis-O-(4-methoxybenzyl)-4-thio-D-arabinofuranosyl)cytosine in 2 mL of dichloromethane, and the obtained mixture was then stirred at room temperature for 1.5 hours. Thereafter, the solvent was distilled away from the reaction mixture under reduced pressure. The obtained residue was purified by silica gel column chromatography (NH column, chloroform/methanol=90/10 to 60/40), so as to obtain 3.1 mg of 1-(2-deoxy-2-fluoro-4-thio-D-arabinofuranosyl)cytosine in the form of a white solid.

Workup

  1. distillationThereafter, the solvent was distilled away from the reaction mixture under reduced pressure
  2. customThe obtained residue was purified by silica gel column chromatography (NH column, chloroform/methanol=90/10 to 60/40)

Sources & evidence

ORD record
ord-e8b76d8067784de58da3b694b9825ab0
Source dataset
uspto-grants-2015_12
Patent number
US09221865B2

Reaction notes

Loading…