Acetic Acid → HCID 57886952, compound

HRID 1819323Notes

Reaction equation

HRID 1819323 reaction equation
[Cl:1][C:2]1[CH:36]=[CH:35][C:34]([F:37])=[CH:33][C:3]=1[CH2:4][N:5]1[C:13]2[C:12](=[O:14])[N:11]([CH3:15])[C:10](=S)[NH:9][C:8]=2[C:7]([C:17]#[N:18])=[C:6]1[N:19]1[CH2:24][CH2:23][CH2:22][C@@H:21]([NH:25][C:26](=[O:32])[O:27][C:28]([CH3:31])([CH3:30])[CH3:29])[CH2:20]1.C(O)(=O)C.O.OO>CO.O.O.[O-][W]([O-])(=O)=O.[Na+].[Na+]>[Cl:1][C:2]1[CH:36]=[CH:35][C:34]([F:37])=[CH:33][C:3]=1[CH2:4][N:5]1[C:13]2[C:12](=[O:14])[N:11]([CH3:15])[CH:10]=[N:9][C:8]=2[C:7]([C:17]#[N:18])=[C:6]1[N:19]1[CH2:24][CH2:23][CH2:22][C@@H:21]([NH:25][C:26](=[O:32])[O:27][C:28]([CH3:31])([CH3:30])[CH3:29])[CH2:20]1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 784Hydrogen PeroxideHCID 962WaterHCID 57886961HCID 57886961, compound

Product 1

HCID 57886952HCID 57886952, compoundYield 113.3%

Reagents, catalysts & solvents 2

HCID 150191Sodium Tungstate DihydrateCatalystHCID 887MethanolSolvent

Procedure

Sodium tungstate dihydrate (0.91 g) was added to a solution of tert-butyl {(3R)-1-[5-(2-chloro-5-fluorobenzyl)-7-cyano-3-methyl-4-oxo-2-thioxo-2,3,4,5-tetrahydro-1H-pyrrolo[3,2-d]pyrimidin-6-yl]piperidin-3-yl}carbamate (1.51 g) in a mixture of methanol (9 ml), acetic acid (3 ml) and water (1 ml), and a 30% aqueous hydrogen peroxide solution (0.29 ml) was added dropwise thereto at room temperature and stirred for 2 hours. After the reaction mixture was allowed to cool, the methanol was distilled off under reduced pressure and the residue was adjusted to pH 9 with an aqueous potassium carbonate solution. A 10% aqueous sodium hydrogensulfite solution was added thereto and stirred for 30 minutes, followed by extraction with ethyl acetate (200 mL). The organic layer was washed with a 10% aqueous potassium carbonate solution and a saturated aqueous sodium chloride solution, dried over sodium sulfate and then filtered and the filtrate was dried under reduced pressure to obtain the title compound (1.61 g).

Workup

  1. temperatureto cool
  2. distillationthe methanol was distilled off under reduced pressure
  3. additionA 10% aqueous sodium hydrogensulfite solution was added
  4. stirringstirred for 30 minutes
  5. extractionfollowed by extraction with ethyl acetate (200 mL)
  6. washThe organic layer was washed with a 10% aqueous potassium carbonate solution
  7. dry with materiala saturated aqueous sodium chloride solution, dried over sodium sulfate
  8. filtrationfiltered
  9. customthe filtrate was dried under reduced pressure

Sources & evidence

ORD record
ord-d1a9891c5e1842a5aad3654ae27af398
Source dataset
uspto-grants-2009_10
Patent number
US07601728B2

Reaction notes

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