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Methanol → methyl 2(S)-ethoxy-3-[4-(2-methylaminothiazol-5-yl)phenyl]propanoate

HRID 910296
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HRID 910296 반응식
[CH2:1]([O:3][C@@H:4]([CH2:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[S:19][C:18]([NH:20][CH3:21])=[N:17][CH:16]=2)=[CH:11][CH:10]=1)[C:5]([OH:7])=[O:6])[CH3:2].[OH-].[Na+].[CH3:24]O>S(=O)(=O)(O)O.O>[CH2:1]([O:3][C@@H:4]([CH2:8][C:9]1[CH:10]=[CH:11][C:12]([C:15]2[S:19][C:18]([NH:20][CH3:21])=[N:17][CH:16]=2)=[CH:13][CH:14]=1)[C:5]([O:7][CH3:24])=[O:6])[CH3:2]
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참가 물질

6

반응물 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 866062382(S)-Ethoxy-3-[4-(2-methylaminothiazol-5-yl)phenyl]propanoic acid

생성물 1

HCID 86606239methyl 2(S)-ethoxy-3-[4-(2-methylaminothiazol-5-yl)phenyl]propanoate수율 67%

시약·촉매·용매 2

HCID 1118Sulfuric Acid촉매
HCID 962
Water
용매

실험 절차

0.5 g (1.6 mmol) of 2(S)-ethoxy-3-[4-(2-methylaminothiazol-5-yl)phenyl]propanoic acid in 10 ml of methanol and a few drops of sulfuric acid is heated at 60° C. for 2 hours. The reaction medium is cooled, diluted with water, neutralized to pH 7 with aqueous 1M sodium hydroxide solution and then extracted with ethyl acetate. The organic phase is washed with saturated sodium chloride solution, dried over magnesium sulfate, filtered and evaporated. The residue obtained is purified by chromatography on a column of silica eluted with a 50/50 heptane/ethyl acetate mixture. 0.34 g (67%) of methyl 2(S)-ethoxy-3-[4-(2-methylaminothiazol-5-yl)phenyl]propanoate is obtained in the form of a yellow solid.

후처리

  1. temperatureThe reaction medium is cooled
  2. extractionextracted with ethyl acetate
  3. washThe organic phase is washed with saturated sodium chloride solution
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue obtained
  8. customis purified by chromatography on a column of silica
  9. washeluted with a 50/50 heptane/ethyl acetate mixture

출처 및 근거

ORD 기록
ord-510f03c5144c42e1898a4addf4573f3e
출처 데이터셋
uspto-grants-2011_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08022079B2

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