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

HRID 885521

反応式

HRID 885521 の反応式
[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]

参加物

8

反応物 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

生成物 1

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

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
-10 °C

実験手順

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+).

後処理

  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

出典と根拠

ORDレコード
ord-18909bd925054872a72a8be1172e91ad
出典データセット
uspto-grants-2012_08
特許番号
US08242174B2

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