Toluene → Uridine pyruvate

HRID 729239

Reaction equation

HRID 729239 reaction equation
[C@@H:1]1([N:10]2[CH:17]=[CH:16][C:14](=[O:15])[NH:13][C:11]2=[O:12])[O:9][C@H:6]([CH2:7][OH:8])[C@@H:4]([OH:5])[C@H:2]1[OH:3].C1(C)C=CC=CC=1.[C:25](Cl)(=[O:29])[C:26]([CH3:28])=[O:27].CO.C(Cl)Cl>CN(C=O)C.N1C=CC=CC=1>[C:25]([O:8][CH2:7][C@H:6]1[O:9][C@@H:1]([N:10]2[CH:17]=[CH:16][C:14](=[O:15])[NH:13][C:11]2=[O:12])[C@H:2]([OH:3])[C@@H:4]1[OH:5])(=[O:29])[C:26]([CH3:28])=[O:27]

Participants

7

Reactant 4

HCID 1140TolueneHCID 6029UridineHCID 5217912-Oxopropanoyl chlorideHCID 21226129Dichloromethane methanol

Product 1

HCID 9879851Uridine pyruvate

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6228DimethylformamideSolvent

Procedure

Uridine (3.0 g, 12 mmol) was dried by toluene azeotrope under vacuum (3×), and then dissolved in DMF (20 mL) and pyridine (20 mL). The resultant solution was cooled to −10 degrees C. and 6.0 mL of pyruvyl chloride (produced in step A above) was added dropwise. The reaction mixture was stirred at room temperature under argon for 24 hours. Analysis by TLC (5% MeOH/CH2Cl2) showed the consumption of uridine. The reaction mixture was evaporated to dryness and partitioned between CH2Cl2 and aqueous sodium bicarbonate. The organic layer was washed with water, aqueous HCl (pH 3.0), and water; dried over sodium sulfate; concentrated; and purified using flash chromatography (silica gel, 5% MeOH/C2Cl2) to yield 1.4 g of uridine pyruvate, or 2′,3′,5′-tri-O-pyruvyluridine.

Workup

  1. customthe consumption of uridine
  2. customThe reaction mixture was evaporated to dryness
  3. custompartitioned between CH2Cl2 and aqueous sodium bicarbonate
  4. washThe organic layer was washed with water, aqueous HCl (pH 3.0), and water
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated
  7. customand purified

Sources & evidence

ORD record
ord-5cb8952656394950ae7fa05c149d5a6a
Source dataset
uspto-grants-2009_09
Patent number
US07582619B2

Linked notes

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