Sodium periodate → HCID 15675992, compound

HRID 1533878Notes

Reaction equation

HRID 1533878 reaction equation
I([O-])(=O)(=O)=[O:2].[Na+].[F:7][C:8]1[C:9]([NH:18][CH2:19][CH:20]2[CH2:25][CH2:24][CH2:23][S:22][CH2:21]2)=[CH:10][C:11]2[O:15][C:14](=[O:16])[NH:13][C:12]=2[CH:17]=1>C(O)C.C1COCC1>[F:7][C:8]1[C:9]([NH:18][CH2:19][CH:20]2[CH2:25][CH2:24][CH2:23][S:22](=[O:2])[CH2:21]2)=[CH:10][C:11]2[O:15][C:14](=[O:16])[NH:13][C:12]=2[CH:17]=1

Participants

5

Reactant 2

HCID 23667635Sodium periodateHCID 67834294HCID 67834294, compound

Product 1

HCID 15675992HCID 15675992, compoundYield 22.1%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

Alumina-supported sodium metaperiodate [K. T. Liu and Y. C. Tong, J.O.C. 43:2717 (1989)] (5.6 g) was added to a solution of 1.2 g (4.25 mmole) 5-fluoro-6-[(tetrahydrothiopyran-3-yl)methylamino]benzoxazolin-2-one in 200 ml ethanol and 50 ml THF. The mixture was stirred for 20 hours at room temperature. The alumina was filtered off and the solvent was removed in vacuo. The crude product was purified by silica gel column chromatography, eluting with ethyl acetate/THF/methanol (80:20:5), and recrystallized from methanol/diethyl ether to give the title compound (0.28 g, 22% yield).

Workup

  1. filtrationThe alumina was filtered off
  2. customthe solvent was removed in vacuo
  3. customThe crude product was purified by silica gel column chromatography
  4. washeluting with ethyl acetate/THF/methanol (80:20:5)
  5. customrecrystallized from methanol/diethyl ether

Sources & evidence

ORD record
ord-3874de94b0fe47ac8ed5671b8e17bc9e
Source dataset
uspto-grants-1992_02
Patent number
US05086062

Reaction notes

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