Cesium carbonate → HCID 178450706, 화합물

HRID 1849676노트

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HRID 1849676 반응식
[CH3:1][C@H:2]1[CH2:7][CH2:6][C@H:5]([CH2:8][OH:9])[CH2:4][CH2:3]1.[Cl:10][C:11]1[C:12](F)=[CH:13][C:14]([F:24])=[C:15]([CH:23]=1)[C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17].C(=O)([O-])[O-].[Cs+].[Cs+]>CS(C)=O.O>[Cl:10][C:11]1[C:12]([O:9][CH2:8][C@H:5]2[CH2:6][CH2:7][C@H:2]([CH3:1])[CH2:3][CH2:4]2)=[CH:13][C:14]([F:24])=[C:15]([CH:23]=1)[C:16]([O:18][C:19]([CH3:20])([CH3:21])[CH3:22])=[O:17]

참가 물질

6

반응물 3

HCID 10796Cesium carbonateHCID 58042499Tert-butyl 5-chloro-2,4-difluorobenzoateHCID 178461264HCID 178461264, 화합물

생성물 1

HCID 178450706HCID 178450706, 화합물수율 78%

시약·촉매·용매 2

HCID 679Dimethyl Sulfoxide용매HCID 962Water용매

반응 조건

온도
70 °C

실험 절차

To a solution of trans-(4-methylcyclohexyl)methanol (3.00 g, 23.4 mmol) and tert-butyl 5-chloro-2,4-difluorobenzoate (6.43 g, 25.90 mmol) in anhydrous dimethylsulfoxide (40 mL) was added cesium carbonate (16.11 g, 49.44 mmol). The mixture was heated at 70° C. for 96 hours, and then cooled to ambient temperature; diluted with water (300 mL) and extracted with ethyl acetate (4×100 mL). The combined organic layers were washed with water (100 mL) and brine (100 mL); dried over anhydrous sodium sulfate; filtered and concentrated in vacuo. The residue was purified by column chromatography (0% to 10% ethyl acetate in hexanes gradient) to give the title compound (6.48 g 78%): 1H NMR (300 MHz, CDCl3) δ 7.87 (d, J=7.7 Hz, 1H), 6.61 (d, J=12.3 Hz, 1H), 3.82 (d, J=6.2 Hz, 2H), 1.91-1.73 (m, 8H), 1.56 (s, 9H), 1.17-0.96 (m, 5H).

후처리

  1. temperaturecooled to ambient temperature
  2. extractionextracted with ethyl acetate (4×100 mL)
  3. washThe combined organic layers were washed with water (100 mL) and brine (100 mL)
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by column chromatography (0% to 10% ethyl acetate in hexanes gradient)

출처 및 근거

ORD 기록
ord-35ed5711d97642cf95628581928abed6
출처 데이터셋
uspto-grants-2015_02
특허 번호
US08952169B2

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