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Water → 2-(3-Fluoro-4-(methylsulfonamidomethyl)phenyl)propanoic acid

HRID 1428728
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HRID 1428728 반응식
[F:1][C:2]1[CH:3]=[C:4]([CH:14]([CH3:20])[C:15]([O:17]CC)=[O:16])[CH:5]=[CH:6][C:7]=1[CH2:8][NH:9][S:10]([CH3:13])(=[O:12])=[O:11].O1CCCC1.O.[OH-].[Li+]>C(OCC)(=O)C.C(O)(=O)C>[F:1][C:2]1[CH:3]=[C:4]([CH:14]([CH3:20])[C:15]([OH:17])=[O:16])[CH:5]=[CH:6][C:7]=1[CH2:8][NH:9][S:10]([CH3:13])(=[O:11])=[O:12]
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참가 물질

7

반응물 4

HCID 962WaterHCID 3939Lithium HydroxideHCID 8028TetrahydrofuranHCID 70855559Ethyl 2-(3-fluoro-4-(methylsulfonamidomethyl)phenyl)propanoate

생성물 1

HCID 866793652-(3-Fluoro-4-(methylsulfonamidomethyl)phenyl)propanoic acid수율 52.4%

시약·촉매·용매 2

HCID 176
Acetic Acid
용매
HCID 8857Ethyl Acetate용매

실험 절차

To a stirred solution of ethyl 2-(3-fluoro-4-(methylsulfonamidomethyl)phenyl)-propanoate (458 mg, 1.51 mmol) in co-solvent with tetrahydrofuran and water (1:1) were added lithium hydroxide (190 mg, 4.529 mmol). The reaction mixture was refluxed for 15 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 was removed in vacuo. The crude was purified by column chromatography to give 2-(3-fluoro-4-(methylsulfonamidomethyl)phenyl)propanoic acid (218 mg, 52%).

후처리

  1. temperatureThe reaction mixture was refluxed for 15 h
  2. washwashed with water and brine
  3. dry with materialThe organic layer was dried over magnesium sulfate
  4. filtrationfiltered
  5. customThe filtrate was removed in vacuo
  6. customThe crude was purified by column chromatography

출처 및 근거

ORD 기록
ord-d4568d27853c40ad9b37d7d6315a4215
출처 데이터셋
uspto-grants-2015_01
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08937092B2

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