Trifluoroacetic acid → 2-Methyl-2-({4-[2-(methyl{5-[4-(trifluoromethoxy)phenyl]pyrimidin-2-yl}amino)ethyl]-1,3-thiazol-2-yl}thio)propionic acid

HRID 914349ノート

反応式

HRID 914349 の反応式
C([O:5][C:6](=[O:37])[C:7]([CH3:36])([S:9][C:10]1[S:11][CH:12]=[C:13]([CH2:15][CH2:16][N:17]([CH3:35])[C:18]2[N:23]=[CH:22][C:21]([C:24]3[CH:29]=[CH:28][C:27]([O:30][C:31]([F:34])([F:33])[F:32])=[CH:26][CH:25]=3)=[CH:20][N:19]=2)[N:14]=1)[CH3:8])(C)(C)C.FC(F)(F)C(O)=O>ClCCl>[CH3:36][C:7]([S:9][C:10]1[S:11][CH:12]=[C:13]([CH2:15][CH2:16][N:17]([CH3:35])[C:18]2[N:23]=[CH:22][C:21]([C:24]3[CH:25]=[CH:26][C:27]([O:30][C:31]([F:32])([F:34])[F:33])=[CH:28][CH:29]=3)=[CH:20][N:19]=2)[N:14]=1)([CH3:8])[C:6]([OH:37])=[O:5]

参加物

4

反応物 2

HCID 6422Trifluoroacetic acidHCID 597593932-Methyl-2-({4-[2-(methyl{5-[4-(trifluoromethoxy)phenyl]pyrimidin-2-yl}amino)ethyl]-1,3-thiazol-2-yl}thio)propionic acid tert-butyl ester

生成物 1

HCID 597589892-Methyl-2-({4-[2-(methyl{5-[4-(trifluoromethoxy)phenyl]pyrimidin-2-yl}amino)ethyl]-1,3-thiazol-2-yl}thio)propionic acid収率 79.5%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

2-Methyl-2-({4-[2-(methyl{5-[4-(trifluoromethoxy)phenyl]pyrimidin-2-yl}amino)ethyl]-1,3-thiazol-2-yl}thio)propionic acid tert-butyl ester (210 mg) obtained in Example 163-1 was dissolved in dichloromethane (2 mL), trifluoroacetic acid (2 mL) was added, and the mixture was stirred at room temperature for 12 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 (the objective compound was 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=2:1 to 1:1) to give the title compound (150 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 (the objective compound
  4. extractionwas 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=2:1 to 1:1)

出典と根拠

ORDレコード
ord-78f4baccb813402c8c08204a83f54cd2
出典データセット
uspto-grants-2011_09
特許番号
US08026370B2

反応ノート

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