HCID 21224211, compound → HCID 21224160, compound

HRID 1584399Notes

Reaction equation

HRID 1584399 reaction equation
[F:1][C:2]1[CH:26]=[CH:25][C:5]([O:6][C:7]2[CH:12]=[CH:11][C:10]([S:13][C:14]3([CH2:20][C:21]([NH:23][OH:24])=[O:22])[CH2:19][CH2:18][O:17][CH2:16][CH2:15]3)=[CH:9][CH:8]=2)=[CH:4][CH:3]=1.[OH:27]OS([O-])=O.[K+]>CO.O>[F:1][C:2]1[CH:3]=[CH:4][C:5]([O:6][C:7]2[CH:8]=[CH:9][C:10]([S:13]([C:14]3([CH2:20][C:21]([NH:23][OH:24])=[O:22])[CH2:19][CH2:18][O:17][CH2:16][CH2:15]3)=[O:27])=[CH:11][CH:12]=2)=[CH:25][CH:26]=1

Participants

5

Reactant 2

HCID 21224211HCID 21224211, compoundHCID 23707502Potassium hydroxy sulfite

Product 1

HCID 21224160HCID 21224160, compoundYield 77.1%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

2-{4-[4-(4-Fluorophenoxy)phenylthio]-tetrahydropyran-4-yl}-N-hydroxyacetamide (500 mg) was dissolved in methanol (25 ml). OXONE (400 mg) in water (5 ml) was added. After stirring for 30 minutes, the mixture was partitioned between methylene chloride and water. Preparative TLC on silica gel and elution with 10% methanol/methylene chloride gave 2-{4-[4-(4-fluorophenoxy)phenylsulfinyl]-tetrahydropyran-4-yl}-N-hydroxyacetamide (402 mg, m.p. 120° C.).

Workup

  1. customthe mixture was partitioned between methylene chloride and water
  2. washPreparative TLC on silica gel and elution with 10% methanol/methylene chloride

Sources & evidence

ORD record
ord-99143a38ce1e4fa3b3b03b2426bfb6af
Source dataset
uspto-grants-1999_08
Patent number
US05932595

Reaction notes

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