Thionyl Chloride → 9-(3,3,3-Trifluoro-2-hydroxy-2-methylpropanoylamino)-4,10-dihydrothieno[3,2-c][1]benzoxepin-10-one

HRID 1824ノート

反応式

HRID 1824 の反応式
[F:1][C:2]([F:10])([F:9])[C:3]([OH:8])([CH3:7])[C:4](O)=[O:5].S(Cl)(Cl)=O.[NH2:15][C:16]1[C:21]2[C:22](=[O:30])[C:23]3[S:29][CH:28]=[CH:27][C:24]=3[CH2:25][O:26][C:20]=2[CH:19]=[CH:18][CH:17]=1>CC(N(C)C)=O.C(OCC)(=O)C>[F:1][C:2]([F:10])([F:9])[C:3]([OH:8])([CH3:7])[C:4]([NH:15][C:16]1[C:21]2[C:22](=[O:30])[C:23]3[S:29][CH:28]=[CH:27][C:24]=3[CH2:25][O:26][C:20]=2[CH:19]=[CH:18][CH:17]=1)=[O:5]

参加物

6

反応物 3

HCID 24386Thionyl ChlorideHCID 27751253,3,3-Trifluoro-2-hydroxy-2-methylpropanoic acidHCID 196930079-Amino-4,10-dihydrothieno[3,2-c][1]benzoxepin-10-one

生成物 1

HCID 196930479-(3,3,3-Trifluoro-2-hydroxy-2-methylpropanoylamino)-4,10-dihydrothieno[3,2-c][1]benzoxepin-10-one収率 89%

試薬・触媒・溶媒 2

HCID 8857Ethyl Acetate溶媒HCID 31374Dimethylacetamide溶媒

実験手順

In dimethylacetamide (3 ml) was dissolved 3,3,3-trifluoro-2-hydroxy-2-methylpropionic acid (0.32 g, 2.03 mmol), and thionyl chloride (148 μl, 2.03 mmol) was added thereto at -15° C., followed by stirring at -15° to -5° C. for one hour. To this reaction mixture was added 9-amino-4,10-dihydrothieno[3,2-c][1]benzoxepin-10-one obtained in Reference Example 11 (0.23 g, 1.02 mmol), and the mixture was stirred overnight at room temperature. After concentration of the reaction mixture under reduced pressure, the obtained oily residue was dissolved in ethyl acetate (20 ml). The organic layer was washed successively with a 5% aqueous solution of sodium bicarbonate and a saturated aqueous solution of sodium chloride, and then dried over anhydrous magnesium sulfate. After the drying agent was filtered off, the organic layer was concentrated under reduced pressure. The obtained oily residue was purified by silica gel column chromatography (hexane/ethyl acetate=5/1), followed by trituration with hexane to give Compound 7 (0.34 g, 89%).

後処理

  1. additionwas added
  2. customat -15° C.
  3. stirringthe mixture was stirred overnight at room temperature
  4. washThe organic layer was washed successively with a 5% aqueous solution of sodium bicarbonate
  5. dry with materiala saturated aqueous solution of sodium chloride, and then dried over anhydrous magnesium sulfate
  6. filtrationAfter the drying agent was filtered off
  7. concentrationthe organic layer was concentrated under reduced pressure
  8. customThe obtained oily residue was purified by silica gel column chromatography (hexane/ethyl acetate=5/1)

出典と根拠

ORDレコード
ord-c07975784c3e442c8e7370feccd7700d
出典データセット
uspto-grants-1998_03
特許番号
US05726325

反応ノート

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