Acetic Acid → HCID 22873853, compound

HRID 716133Notes

Reaction equation

HRID 716133 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-7af3be64889c4e98b3b55311be660e40
Source dataset
uspto-grants-2015_11
Patent number
US09187514B2

Reaction notes

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