HCID 44322635, compound → HCID 44322636, compound

HRID 343356Notes

Reaction equation

HRID 343356 reaction equation
C([O:5][C:6](/[CH:8]=[CH:9]/[C:10]1[N:18]([CH3:19])[C:17]2[C:16](=[O:20])[N:15]([CH3:21])[C:14](=[O:22])[N:13]([CH3:23])[C:12]=2[N:11]=1)=[O:7])(C)(C)C>C(O)(C(F)(F)F)=O>[C:6](/[CH:8]=[CH:9]/[C:10]1[N:18]([CH3:19])[C:17]2[C:16](=[O:20])[N:15]([CH3:21])[C:14](=[O:22])[N:13]([CH3:23])[C:12]=2[N:11]=1)([OH:7])=[O:5]

Participants

3

Reactant 1

HCID 44322635HCID 44322635, compound

Product 1

HCID 44322636HCID 44322636, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

8-(trans-2-tert-Butyloxycarbonylvinyl)-1,3,7-trimethylxanthine (76 mg, 238 μmol) was dissolved in 3 ml TFA and stirred for 1 h. After evaporation, the residue was triturated with ether to provide the pure product 8-(trans-2-Carboxyvinyl)-1,3,7-trimethylxanthine (55 mg, 88% yield). mp: 278d °C. 1H NMR DMSO-d6 : d 3.27 (s, 3H, NCH3), 3.44 (s, 3H, NCH3), 4.02 (s, 3H N7CH3), 6.78 (d, 1H, J=15.4 Hz), 7.55 (d, 1H, J=15.4 Hz), 8.4 (br s, 1H, COOH). MS (CI NH3) m/e 265 (MH+). Alternatively, compound 8-(trans-2-Carboxyvinyl)-1,3,7-trimethylxanthine was prepared from 8-(trans-2-tert-Butyloxycarbonylvinyl)-1,3,7-trimethylxanthine in DMF/water (1:1) solution by saponification with sodium hydroxide in 49% yield.

Workup

  1. customAfter evaporation
  2. customthe residue was triturated with ether

Sources & evidence

ORD record
ord-cb6176d6eae047139de1a36e60abe9a1
Source dataset
uspto-grants-1999_01
Patent number
US05861405

Reaction notes

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