N-hydroxy-2-[1-(4-phenoxyphenylthio)-cyclopent-1-yl]-acetamide → N-hydroxy-2-[1-(4-phenoxyphenylsulfinyl)-cyclopent-1-yl]-acetamide

HRID 1584398Notes

Reaction equation

HRID 1584398 reaction equation
[OH:1][NH:2][C:3](=[O:24])[CH2:4][C:5]1([S:10][C:11]2[CH:16]=[CH:15][C:14]([O:17][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)=[CH:13][CH:12]=2)[CH2:9][CH2:8][CH2:7][CH2:6]1.I([O-])(=O)(=O)=[O:26].[Na+]>CC(C)=O.O.C(Cl)Cl>[OH:1][NH:2][C:3](=[O:24])[CH2:4][C:5]1([S:10]([C:11]2[CH:16]=[CH:15][C:14]([O:17][C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=3)=[CH:13][CH:12]=2)=[O:26])[CH2:9][CH2:8][CH2:7][CH2:6]1

Participants

6

Reactant 2

HCID 21224318N-hydroxy-2-[1-(4-phenoxyphenylthio)-cyclopent-1-yl]-acetamideHCID 23667635Sodium periodate2×

Product 1

HCID 21224342N-hydroxy-2-[1-(4-phenoxyphenylsulfinyl)-cyclopent-1-yl]-acetamideYield 31.8%

Reagents, catalysts & solvents 3

HCID 180AcetoneSolventHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of N-hydroxy-2-[1-(4-phenoxyphenylthio)-cyclopent-1-yl]-acetamide (45 mg) in acetone (4 ml) was treated with sodium periodate (260 mg) in water (2 ml). Over the course of 24 hours, two additional portions of sodium periodate (260 mg) were added. After complete disappearance of starting material the solution was diluted with methylene chloride, filtered, dried, and the solvent evaporated under reduced pressure. Preparative TLC on silica gel and elution with 10% methanol/methylene chloride gave N-hydroxy-2-[1-(4-phenoxyphenylsulfinyl)-cyclopent-1-yl]-acetamide (15 mg), PMR (CDCl3) 7.64 (d,2H), 7.44 (t,2H), 7.30-7.05 (m,5H), 2.97 (d,1H), 2.53 (d,1H), 2.15-1.65 (m,8H).

Workup

  1. filtrationfiltered
  2. customdried
  3. customthe solvent evaporated under reduced pressure
  4. washPreparative TLC on silica gel and elution with 10% methanol/methylene chloride

Sources & evidence

ORD record
ord-8d8e33c3bf16474ab092112ab33254d8
Source dataset
uspto-grants-1999_08
Patent number
US05932595

Reaction notes

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