Sulfuric Acid → Ethyl [(6S)-6-(3,5-difluorophenyl)-3,3-dimethyl-2,4-dioxopiperidin-1-yl]acetate

HRID 1866658노트

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HRID 1866658 반응식
[F:1][C:2]1[CH:3]=[C:4]([C@H:9]2[N:14]([CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17])[C:13](=[O:21])[C:12]([CH3:23])([CH3:22])[C@@H:11]([OH:24])[CH2:10]2)[CH:5]=[C:6]([F:8])[CH:7]=1.OS(O)(=O)=O>CC(C)=O.O.[O-2].[O-2].[O-2].[Cr+6]>[F:1][C:2]1[CH:3]=[C:4]([C@H:9]2[N:14]([CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17])[C:13](=[O:21])[C:12]([CH3:23])([CH3:22])[C:11](=[O:24])[CH2:10]2)[CH:5]=[C:6]([F:8])[CH:7]=1

참가 물질

6

반응물 2

HCID 1118Sulfuric AcidHCID 86616394HCID 86616394, 화합물2회

생성물 1

HCID 86616396Ethyl [(6S)-6-(3,5-difluorophenyl)-3,3-dimethyl-2,4-dioxopiperidin-1-yl]acetate

시약·촉매·용매 3

HCID 10219390chromium (VI) trioxide촉매HCID 180Acetone용매HCID 962Water용매

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온도
0 °C

실험 절차

To a solution of ethyl [(4S,6S)-6-(3,5-difluorophenyl)-4-hydroxy-3,3-dimethyl-2-oxopiperidin-1-yl]acetate (470 mg, 1.377 mmol, described in Intermediate 21) in acetone (24 mL) at 0° C. was added a solution of chromium (VI) trioxide (174 mg, 1.740 mmol) in H2O (0.5 mL) and H2SO4 (0.147 mL, 2.75 mmol), in three portions over 5 min and the mixture was stirred at 0° C. for 30 min. Most of the acetone was removed by concentration in vacuo, and the residue was basified with saturated aqueous NaHCO3 (75 mL) and extracted with EtOAc (2×100 mL). The combined organic layers were washed with brine (40 mL) and dried over Na2SO4, filtered, and concentrated in vacuo. The crude product was purified by silica gel chromatography, eluting with a gradient of CH2Cl2:CH3OH—100:0 to 92:8, to give the title compound. MS: m/z=340 (M+1).

후처리

  1. customMost of the acetone was removed by concentration in vacuo
  2. extractionextracted with EtOAc (2×100 mL)
  3. washThe combined organic layers were washed with brine (40 mL)
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe crude product was purified by silica gel chromatography
  8. washeluting with a gradient of CH2Cl2

출처 및 근거

ORD 기록
ord-69a7cdb2f6b54d1b9c9972eb3e664c66
출처 데이터셋
uspto-grants-2009_12
특허 번호
US07629338B2

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