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Trifluoroacetic acid → 2-[(4-{2-[Heptyl(5-morpholin-4-ylpyrimidin-2-yl)amino]ethyl}-1,3-thiazol-2-yl)thio]-2-methylpropionic acid

HRID 914371
ノート
印刷プレビュー

反応式

HRID 914371 の反応式
C([O:5][C:6](=[O:38])[C:7]([S:10][C:11]1[S:12][CH:13]=[C:14]([CH2:16][CH2:17][N:18]([CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH3:37])[C:19]2[N:24]=[CH:23][C:22]([N:25]3[CH2:30][CH2:29][O:28][CH2:27][CH2:26]3)=[CH:21][N:20]=2)[N:15]=1)([CH3:9])[CH3:8])(C)(C)C.FC(F)(F)C(O)=O>ClCCl>[CH2:31]([N:18]([C:19]1[N:20]=[CH:21][C:22]([N:25]2[CH2:26][CH2:27][O:28][CH2:29][CH2:30]2)=[CH:23][N:24]=1)[CH2:17][CH2:16][C:14]1[N:15]=[C:11]([S:10][C:7]([CH3:8])([CH3:9])[C:6]([OH:38])=[O:5])[S:12][CH:13]=1)[CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH3:37]
参加物実験手順後処理出典と根拠反応ノート

参加物

4

反応物 2

HCID 6422Trifluoroacetic acidHCID 597591682-[(4-{2-[Heptyl(5-morpholin-4-ylpyrimidin-2-yl)amino]ethyl}-1,3-thiazol-2-yl)thio]-2-methylpropionic acid tert-butyl ester

生成物 1

HCID 248639972-[(4-{2-[Heptyl(5-morpholin-4-ylpyrimidin-2-yl)amino]ethyl}-1,3-thiazol-2-yl)thio]-2-methylpropionic acid収率 46.9%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

2-[(4-{2-[Heptyl(5-morpholin-4-ylpyrimidin-2-yl)amino]ethyl}-1,3-thiazol-2-yl)thio]-2-methylpropionic acid tert-butyl ester (710 mg) obtained in Example 442-2 was dissolved in dichloromethane (4 mL), trifluoroacetic acid (4 mL) was added, and the mixture was stirred at room temperature for 20 hr. The reaction mixture was concentrated under reduced pressure, ethyl acetate was added, and the mixture was washed with saturated aqueous sodium hydrogen carbonate solution (at this time point, the object product had been extracted in the ethyl acetate layer). The ethyl acetate layer was washed with aqueous 10% citric acid solution and saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel chromatography (elution solvent; hexane:ethyl acetate=1:1 to 0:1) to give the title compound (300 mg) as a white solid.

後処理

  1. concentrationThe reaction mixture was concentrated under reduced pressure, ethyl acetate
  2. additionwas added
  3. washthe mixture was washed with saturated aqueous sodium hydrogen carbonate solution (at this time point
  4. extractionthe object product had been extracted in the ethyl acetate layer)
  5. washThe ethyl acetate layer was washed with aqueous 10% citric acid solution and saturated brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. customThe solvent was evaporated under reduced pressure
  8. customthe residue was purified by silica gel chromatography (elution solvent; hexane:ethyl acetate=1:1 to 0:1)

出典と根拠

ORDレコード
ord-9bb9e73727b743638c87a28183165334
出典データセット
uspto-grants-2011_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08026370B2

反応ノート

読み込み中…

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