Trifluoroacetic acid → HCID 54112621, compound

HRID 716121Notes

Reaction equation

HRID 716121 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-aaeb96fcc1c444b1a1443a99d405ad4b
Source dataset
uspto-grants-2015_11
Patent number
US09187514B2

Reaction notes

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