p-Toluenesulfonic acid → 362-75-4

HRID 1787982Notes

Reaction equation

HRID 1787982 reaction equation
[C:1]1(C)[CH:6]=CC(S(O)(=O)=O)=C[CH:2]=1.[C@@H:12]1([N:21]2[C:30]3[N:29]=[CH:28][N:27]=[C:25]([NH2:26])[C:24]=3[N:23]=[CH:22]2)[O:20][C@H:17]([CH2:18][OH:19])[C@@H:15]([OH:16])[C@H:13]1[OH:14].COC(OC)(C)C.[OH-].[NH4+]>CC(C)=O.C(Cl)Cl.C(O)C>[CH3:2][C:1]1([CH3:6])[O:14][C@@H:13]2[C@@H:15]([C@@H:17]([CH2:18][OH:19])[O:20][C@H:12]2[N:21]2[C:30]3[N:29]=[CH:28][N:27]=[C:25]([NH2:26])[C:24]=3[N:23]=[CH:22]2)[O:16]1

Participants

7

Reactant 4

HCID 6101p-Toluenesulfonic acidHCID 64952,2-DimethoxypropaneHCID 14923Ammonium HydroxideHCID 60961Adenosine

Product 1

HCID 2723654362-75-4Yield 87.7%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolvent2×HCID 21584144Dichloromethane ethanolSolvent

Procedure

A solution of p-toluenesulfonic acid (7.79 g, 0.45 mol) in dry acetone (100 ml) is added dropwise to a solution of adenosine (10 g, 0.037 mol) in dry acetone (300 ml). 2,2-Dimethoxypropane (18.18 ml, d=0.847) is then added to the reaction mixture, and the mixture stirred for 48 hours (TLC methylene chloride/ethanol 9:1). The solution slowly becomes clear and is made basic with 3% ammonium hydroxide (800 ml). The solvent is removed at reduced pressure, keeping the temperature below 30° C. until formation of a solid that is collected by filtration. This procedure is repeated several times by concentrating the filtrate. A white solid is obtained (10.08 g, 0.0328 mol, 87.7% yield).

Workup

  1. customThe solvent is removed at reduced pressure
  2. customthe temperature below 30° C.
  3. filtrationthat is collected by filtration
  4. concentrationby concentrating the filtrate
  5. customA white solid is obtained (10.08 g, 0.0328 mol, 87.7% yield)

Sources & evidence

ORD record
ord-e70bcd291c9e4b55bba3424621298b37
Source dataset
uspto-grants-2009_03
Patent number
US07511133B2

Reaction notes

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