Acetic Acid → HCID 22873853, compound

HRID 1508629Notes

Reaction equation

HRID 1508629 reaction equation
C[O-].[Na+].CO.C([O:14][C@@H:15]1[C@H:19]([O:20]C(=O)C2C=CC=CC=2)[C@@H:18]([CH2:29][O:30]C(=O)C2C=CC=CC=2)[S:17][C@H:16]1[N:39]1[CH:46]=[CH:45][C:43]([NH2:44])=[N:42][C:40]1=[O:41])(=O)C1C=CC=CC=1.C(O)(=O)C>CO>[C@@H:16]1([N:39]2[CH:46]=[CH:45][C:43]([NH2:44])=[N:42][C:40]2=[O:41])[S:17][C@H:18]([CH2:29][OH:30])[C@@H:19]([OH:20])[C@H:15]1[OH:14]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 23694274Sodium methanolate methanolHCID 89975769HCID 89975769, compound

Product 1

HCID 22873853HCID 22873853, compoundYield 56.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

0.1 mL of a 28% sodium methoxide/methanol solution was added to a suspension of 70 mg of 1-(2,3,5-tri-O-benzoyl-4-thio-β-D-ribofuranosyl)cytosine in 2.0 mL of methanol, and the obtained mixture was then stirred at room temperature for 1 hour and was then left overnight. Thereafter, 0.2 mL of acetic acid was added to the reaction mixture, and the solvent was then distilled away under reduced pressure. The obtained residue was purified by silica gel column chromatography (ethyl acetate/methanol=1/0 to 2/1), so as to obtain 18 mg of 1-(4-thio-β-D-ribofuranosyl)cytosine in the form of a white solid.

Workup

  1. waitwas then left overnight
  2. distillationthe solvent was then distilled away under reduced pressure
  3. customThe obtained residue was purified by silica gel column chromatography (ethyl acetate/methanol=1/0 to 2/1)

Sources & evidence

ORD record
ord-4e7c186a92704de59282ddce232ae22d
Source dataset
uspto-grants-2015_12
Patent number
US09221865B2

Reaction notes

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