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Water → 2-(4-(Methylsulfonamidomethyl)phenyl)propanoic acid

HRID 1428714
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HRID 1428714 반응식
[CH3:1][S:2]([NH:5][CH2:6][C:7]1[CH:12]=[CH:11][C:10]([CH:13]([CH3:19])[C:14]([O:16]CC)=[O:15])=[CH:9][CH:8]=1)(=[O:4])=[O:3].O1CCCC1.O.[OH-].[Na+]>C(OCC)(=O)C.C(O)(=O)C>[CH3:1][S:2]([NH:5][CH2:6][C:7]1[CH:12]=[CH:11][C:10]([CH:13]([CH3:19])[C:14]([OH:16])=[O:15])=[CH:9][CH:8]=1)(=[O:4])=[O:3]
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참가 물질

7

반응물 4

HCID 962WaterHCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 70816013Ethyl 2-(4-(methylsulfonamidomethyl)phenyl)propanoate

생성물 1

HCID 708161912-(4-(Methylsulfonamidomethyl)phenyl)propanoic acid수율 25.2%

시약·촉매·용매 2

HCID 176Acetic Acid
용매
HCID 8857Ethyl Acetate용매

실험 절차

To a stirred solution of ethyl 2-(4-(methylsulfonamidomethyl)phenyl)propanoate (325 mg, 1.139 mmol) in co-solvent with tetrahydrofuran and water (1:1) were added sodium hydroxide (114 mg, 2.8475 mmol). The reaction mixture was refluxed for 16 h, then cooled to room temperature, acidified to pH 3-4 with acetic acid. The residue dissolved in ethyl acetate and washed with water and brine. The organic layer was dried over magnesium sulfate and filtered. The filtrate removed in vacuo. The crude was purified by column chromatography to give 2-(4-(methylsulfonamidomethyl)phenyl)propanoic acid (74 mg, 25%).

후처리

  1. temperatureThe reaction mixture was refluxed for 16 h
  2. washwashed with water and brine
  3. dry with materialThe organic layer was dried over magnesium sulfate
  4. filtrationfiltered
  5. customThe filtrate removed in vacuo
  6. customThe crude was purified by column chromatography

출처 및 근거

ORD 기록
ord-d8ba9ad310874a7da244fc4c004ecfe3
출처 데이터셋
uspto-grants-2015_01
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08937092B2

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