Sodium periodate → HCID 178432825, compound

HRID 1838638Notes

Reaction equation

HRID 1838638 reaction equation
[OH:1][C:2]1[CH:8]2[CH:6]([CH2:7]2)[C:5]([CH3:11])([S:9][CH3:10])[C:4](=[O:12])[C:3]=1[C:13]([C:15]1[C:16]([CH3:25])=[N:17][C:18]([C:21]([F:24])([F:23])[F:22])=[CH:19][CH:20]=1)=[O:14].I([O-])(=O)(=O)=[O:27].[Na+]>CO>[OH:1][C:2]1[CH:8]2[CH:6]([CH2:7]2)[C:5]([S:9]([CH3:10])=[O:27])([CH3:11])[C:4](=[O:12])[C:3]=1[C:13]([C:15]1[C:16]([CH3:25])=[N:17][C:18]([C:21]([F:24])([F:23])[F:22])=[CH:19][CH:20]=1)=[O:14]

Participants

4

Reactant 2

HCID 23667635Sodium periodateHCID 178503299HCID 178503299, compound

Product 1

HCID 178432825HCID 178432825, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

0.87 g (2.3 mmol) of 5-hydroxy-2-methyl-2-methylsulfanyl-4-(2-methyl-6-trifluoromethylpyridine-3-carbonyl)bicyclo[4.1.0]hept-4-en-3-one (compound A2-D 113), dissolved in 8 ml of methanol, is warmed for 3 hours at a temperature of 50° C. in the presence of 0.56 g of sodium periodate. The mixture is then partitioned between ethyl acetate and sodium chloride solution, concentrated, and the crude product is purified by chromatography (mobile phase: ethyl acetate/methanol 19:1). Pure 5-hydroxy-2-methanesulfinyl-2-methyl-4-(2-methyl-6-trifluoromethylpyridine-3-carbonyl)bicyclo[4.1.0]hept-4-en-3-one is obtained as tautomer and isomer mixture of melting point 159.5-160° C.

Workup

  1. customThe mixture is then partitioned between ethyl acetate and sodium chloride solution
  2. concentrationconcentrated
  3. customthe crude product is purified by chromatography (mobile phase: ethyl acetate/methanol 19:1)

Sources & evidence

ORD record
ord-103fd47a976841fbbee3c32426cb90e5
Source dataset
uspto-grants-2004_01
Patent number
US06673938B1

Reaction notes

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