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

HRID 1584398
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HRID 1584398 반응식
[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
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참가 물질

6

반응물 2

HCID 21224318N-hydroxy-2-[1-(4-phenoxyphenylthio)-cyclopent-1-yl]-acetamideHCID 23667635Sodium periodate2회

생성물 1

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

시약·촉매·용매 3

HCID 180Acetone용매HCID 962Water용매
HCID 6344
Dichloromethane
용매

실험 절차

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).

후처리

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

출처 및 근거

ORD 기록
ord-8d8e33c3bf16474ab092112ab33254d8
출처 데이터셋
uspto-grants-1999_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05932595

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