2,2-Dimethoxypropane → 5'-Deoxy-2',3'-O-isopropylidene-5-fluorocytidine

HRID 1089413Notes

Reaction equation

HRID 1089413 reaction equation
[F:1][C:2]1[C:3]([NH2:17])=[N:4][C:5](=[O:16])[N:6]([CH:15]=1)[C@@H:7]1[O:14][C@H:12]([CH3:13])[C@@H:10]([OH:11])[C@H:8]1[OH:9].O.[C:19]1(C)[CH:24]=CC(S(O)(=O)=O)=C[CH:20]=1.COC(OC)(C)C.C(=O)([O-])O.[Na+]>CC(C)=O>[CH3:13][C@H:12]1[O:14][C@@H:7]([N:6]2[C:5](=[O:16])[N:4]=[C:3]([NH2:17])[C:2]([F:1])=[CH:15]2)[C@@H:8]2[O:9][C:19]([CH3:24])([CH3:20])[O:11][C@H:10]12

Participants

6

Reactant 4

HCID 64952,2-DimethoxypropaneHCID 516892Sodium BicarbonateHCID 521998p-Toluenesulfonic acid monohydrateHCID 100374995'-Deoxy-5-fluorocytidine

Product 1

HCID 130663685'-Deoxy-2',3'-O-isopropylidene-5-fluorocytidineYield 100%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A solution of 5'-deoxy-5-fluorocytidine (490 mg), p-toluenesulfonic acid monohydrate (418 mg) and 2,2-dimethoxypropane (984 μl) in acetone (10 ml) was stirred for 1.5 hour at room temperature. To the solution was added sodium hydrogen carbonate (900 mg) and the mixture was stirred for 4 hours at room temperature. The precipitate was filtered off and washed with acetone. The combined filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (dichloromethane-methanol) to give 5'-deoxy-5-fluoro-2',3'-O-isopropylidenecytidine (570 mg). MS 286 (MH+); mp of the picrate 169°~171° C.

Workup

  1. filtrationThe precipitate was filtered off
  2. washwashed with acetone
  3. concentrationThe combined filtrate was concentrated under reduced pressure
  4. customThe residue was purified by silica gel column chromatography (dichloromethane-methanol)

Sources & evidence

ORD record
ord-3238627eff4949ec8b844d778ab77862
Source dataset
uspto-grants-1990_10
Patent number
US04966891

Reaction notes

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