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

HRID 910296
ノート
印刷プレビュー

反応式

HRID 910296 の反応式
[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]
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 1118Sulfuric Acid触媒
HCID 962
Water
溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-510f03c5144c42e1898a4addf4573f3e
出典データセット
uspto-grants-2011_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08022079B2

反応ノート

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