Hydrochloric Acid → 5'-Deoxy-5-ethenylcytidine

HRID 321935Notes

Reaction equation

HRID 321935 reaction equation
C([O:4][C@@H:5]1[C@H:9]([O:10]C(=O)C)[C@@H:8]([CH3:14])[O:7][C@H:6]1[N:15]1[CH:22]=[C:21]([CH:23]=[CH2:24])[C:19]([NH2:20])=[N:18][C:16]1=[O:17])(=O)C.[OH-].[Na+].Cl>CO>[CH:23]([C:21]1[C:19]([NH2:20])=[N:18][C:16](=[O:17])[N:15]([CH:22]=1)[C@@H:6]1[O:7][C@H:8]([CH3:14])[C@@H:9]([OH:10])[C@H:5]1[OH:4])=[CH2:24]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 9840745HCID 9840745, compound

Product 1

HCID 544377885'-Deoxy-5-ethenylcytidineYield 98%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 2′,3′-di-O-acetyl-5′-deoxy-5-vinylcytidine (111 mg, 3.29 mmol) in 5 ml of methanol was added 1N NaOH (0.32 ml, 0.32 mmol) at room temperature. After stirring for 1 hour, 1 N HCl (ca.0.3 ml) was added to the reaction mixture, and then the reaction mixture was concentrated under reduced pressure. The residue was purified by solid phase extraction (MEGA Bond Elute LRC, eluent:H2O˜H2O:MeOH=1:1, step gradient) to give 5′-deoxy-5-vinylcytidine (82 mg, 98%) as colorless solid:

Workup

  1. concentrationthe reaction mixture was concentrated under reduced pressure
  2. customThe residue was purified by solid phase extraction (MEGA Bond Elute LRC, eluent:H2O˜H2O:MeOH=1:1, step gradient)

Sources & evidence

ORD record
ord-e00dc351156d4d0185dd2cdabdb837b4
Source dataset
uspto-grants-2001_04
Patent number
US06211166B1

Reaction notes

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