2,2-Dimethoxypropane → 362-43-6

HRID 1760919Notes

Reaction equation

HRID 1760919 reaction equation
N([C@:4]1([CH2:19][OH:20])[O:8][C@@H:7]([N:9]2[CH:16]=[CH:15][C:13](=[O:14])[NH:12][C:10]2=[O:11])[C@H:6]([OH:17])[C@@H:5]1[OH:18])=[N+]=[N-].CO[C:23](OC)([CH3:25])[CH3:24]>CC(C)=O.C(OCC)(=O)C.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>[OH:20][CH2:19][CH:4]1[CH:5]2[O:18][C:23]([CH3:25])([CH3:24])[O:17][CH:6]2[CH:7]([N:9]2[CH:16]=[CH:15][C:13](=[O:14])[NH:12][C:10]2=[O:11])[O:8]1

Participants

6

Reactant 2

HCID 64952,2-DimethoxypropaneHCID 4538284'-Azidouridine

Product 1

HCID 351234362-43-6Yield 73.7%

Reagents, catalysts & solvents 3

HCID 521998p-Toluenesulfonic acid monohydrateCatalystHCID 180AcetoneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture containing 3.0 g (10.5 mmol) of 4′-azidouridine, 0.05 g (0.26 mmol) p-toluenesulfonic acid monohydrate and 6 mL (48.8 mmol) 2,2-dimethoxypropane in 20 mL acetone was stirred at room temperature for 12 h. The reaction mixture was diluted with ethyl acetate, washed with saturated aqueous sodium hydrogen carbonate solution, dried over magnesium sulfate and evaporated to dryness under reduced pressure to give the desired product 2.20 g (64%) of as a white solid.

Workup

  1. washwashed with saturated aqueous sodium hydrogen carbonate solution
  2. dry with materialdried over magnesium sulfate
  3. customevaporated to dryness under reduced pressure

Sources & evidence

ORD record
ord-f5e80d77246946559beea817c48bf034
Source dataset
uspto-grants-2005_01
Patent number
US06846810B2

Reaction notes

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