Sodium periodate → 3-(4,4-Dibutyl-7-fluoro-1-hydroxy-3-oxo-3,4-dihydronaphthalen-2-yl)-4h-1,2,4-benzothiadiazine-7-carbaldehyde 1,1-dioxide

HRID 494495Notes

Reaction equation

HRID 494495 reaction equation
[CH2:1]([C:5]1([CH2:32][CH2:33][CH2:34][CH3:35])[C:14]2[C:9](=[CH:10][C:11]([F:15])=[CH:12][CH:13]=2)[C:8]([OH:16])=[C:7]([C:17]2[NH:22][C:21]3[CH:23]=[CH:24][C:25]([CH:27]=C)=[CH:26][C:20]=3[S:19](=[O:30])(=[O:29])[N:18]=2)[C:6]1=[O:31])[CH2:2][CH2:3][CH3:4].I([O-])(=O)(=O)=[O:37].[Na+]>O1CCOCC1.O.C(O)(C)(C)C.[Cl-].[NH4+].[Os](=O)(=O)(=O)=O>[CH2:32]([C:5]1([CH2:1][CH2:2][CH2:3][CH3:4])[C:14]2[C:9](=[CH:10][C:11]([F:15])=[CH:12][CH:13]=2)[C:8]([OH:16])=[C:7]([C:17]2[NH:22][C:21]3[CH:23]=[CH:24][C:25]([CH:27]=[O:37])=[CH:26][C:20]=3[S:19](=[O:30])(=[O:29])[N:18]=2)[C:6]1=[O:31])[CH2:33][CH2:34][CH3:35]

Participants

8

Reactant 2

HCID 23667635Sodium periodateHCID 1364036701,1-Dibutyl-3-(1,1-dioxido-7-vinyl-4h-1,2,4-benzothiadiazin-3-yl)-6-fluoro-4-hydroxynaphthalen-2(1h)-one

Product 1

HCID 1354367413-(4,4-Dibutyl-7-fluoro-1-hydroxy-3-oxo-3,4-dihydronaphthalen-2-yl)-4h-1,2,4-benzothiadiazine-7-carbaldehyde 1,1-dioxideYield 94.3%

Reagents, catalysts & solvents 5

HCID 30318Osmium TetroxideCatalystHCID 962WaterSolvent2×HCID 6386tert-ButanolSolventHCID 25517Ammonium ChlorideSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution of the compound of Example 21A (52 mg, 0.10 mmol) in dioxane (2 mL) and water (200 μL) was treated with a solution of osmium tetroxide in t-butanol (2.5% (wt/vol), 200 μL) and sodium periodate (45 mg, 0.21 mmol) followed by stirring at ambient temperature for 24 h. The mixture was diluted with water and saturated ammonium chloride solution. The mixture was extracted with ethyl acetate and the organic layer washed with water and saturated NaCl solution. Drying (Na2SO4) and concentration in vacuo afforded the title compound (47 mg, 90%) as a white solid. 1H NMR (300 MHz, DMSO-d6): δ 0.51 (m, 2H) 0.69 (t, J=7.35 Hz, 6 H) 0.90 (m, 2 H) 1.10 (m, 4 H) 1.92 (m, 2 H) 2.15 (m, 2 H) 7.52 (m, 1 H) 7.73 (m, 3 H) 8.11 (dd, J=8.64, 1.65 Hz, 1 H) 8.40 (d, J=1.47 Hz, 1 H) 10.03 (s, 1 H) 14.38 (s, 1 H).

Workup

  1. extractionThe mixture was extracted with ethyl acetate
  2. washthe organic layer washed with water and saturated NaCl solution
  3. customDrying
  4. concentration(Na2SO4) and concentration in vacuo

Sources & evidence

ORD record
ord-ff84ca90ddf64890963992f913ba73f1
Source dataset
uspto-grants-2009_05
Patent number
US07538105B2

Reaction notes

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