Triethylamine → (R)-3-(8-(4-fluoro-3-methylphenyl)octanoyl)-4-isopropyloxazolidin-2-one

HRID 885521

반응식

HRID 885521 반응식
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][C:15]([OH:17])=O)=[CH:4][C:3]=1[CH3:18].C(N(CC)CC)C.C(Cl)(=O)C(C)(C)C.[Li+].[Cl-].[CH:35]([C@@H:38]1[CH2:42][O:41][C:40](=[O:43])[NH:39]1)([CH3:37])[CH3:36]>C1COCC1.C(OCC)(=O)C>[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][C:15]([N:39]2[C@H:38]([CH:35]([CH3:37])[CH3:36])[CH2:42][O:41][C:40]2=[O:43])=[O:17])=[CH:4][C:3]=1[CH3:18]

참가 물질

8

반응물 5

HCID 8471TriethylamineHCID 62493Pivaloyl chlorideHCID 433294Lithium ChlorideHCID 641505(4R)-4-(Propan-2-yl)-1,3-oxazolidin-2-oneHCID 595125948-(4-Fluoro-3-methylphenyl)octanoic acid

생성물 1

HCID 69169742(R)-3-(8-(4-fluoro-3-methylphenyl)octanoyl)-4-isopropyloxazolidin-2-one수율 82.1%

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매

반응 조건

온도
-10 °C

실험 절차

To a cooled (−10° C.) solution of 8-(4-fluoro-3-methylphenyl)octanoic acid (0.486 g, 1.926 mmol) in 15 mL of THF, were added stepwise triethylamine (0.69 mL, 4.952 mmol) and pivaloyl chloride (0.23 mL, 1.889 mmol). The reaction mixture was stirred at −10° C. for 1 h and then LiCl (0.080 g, 1.889 mmol) and (R)-4-iso-propyloxazolidin-2-one (0.237 g, 1.834 mmol) were added stepwise. After being warmed slowly to room temperature and stirred for overnight, the reaction mixture was diluted with ethyl acetate (80 mL) and washed with saturated NaHCO3 solution and brine. The organic layer was dried (Na2SO4), filtered, and concentrated under reduced pressure. The product was isolated by Flash column chromatography (silica gel column) eluting with 0-100% dichloromethane/hexanes to give the title compound as colorless oil (0.547 g, 82% yield). GC-MS: tR=6.9 min; m/z 363 (M+).

후처리

  1. temperatureAfter being warmed slowly to room temperature
  2. stirringstirred for overnight
  3. washwashed with saturated NaHCO3 solution and brine
  4. dry with materialThe organic layer was dried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe product was isolated by Flash column chromatography (silica gel column)
  8. washeluting with 0-100% dichloromethane/hexanes

출처 및 근거

ORD 기록
ord-18909bd925054872a72a8be1172e91ad
출처 데이터셋
uspto-grants-2012_08
특허 번호
US08242174B2

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