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

HRID 1824노트

반응식

HRID 1824 반응식
[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]

참가 물질

6

반응물 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

생성물 1

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

시약·촉매·용매 2

HCID 8857Ethyl Acetate용매HCID 31374Dimethylacetamide용매

실험 절차

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%).

후처리

  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)

출처 및 근거

ORD 기록
ord-c07975784c3e442c8e7370feccd7700d
출처 데이터셋
uspto-grants-1998_03
특허 번호
US05726325

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