Dimethyl Sulfoxide → tert-Butyl 4-fluoro-5-oxoazepane-1-carboxylate

HRID 876414ノート

反応式

HRID 876414 の反応式
[F:1][C:2]1(C(OCC)=O)[C:8](=[O:9])[CH2:7][CH2:6][N:5]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH2:4][CH2:3]1.CS(C)=O.O.[Li+].[Cl-]>CCOC(C)=O>[F:1][CH:2]1[C:8](=[O:9])[CH2:7][CH2:6][N:5]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH2:4][CH2:3]1

参加物

6

反応物 4

HCID 679Dimethyl SulfoxideHCID 962WaterHCID 433294Lithium ChlorideHCID 672338451-Tert-butyl 4-ethyl 4-fluoro-5-oxoazepane-1,4-dicarboxylate

生成物 1

HCID 67230220tert-Butyl 4-fluoro-5-oxoazepane-1-carboxylate収率 56%

試薬・触媒・溶媒 1

HCID 8857Ethyl Acetate溶媒

反応条件

温度
125 °C

実験手順

To a 500 mL flask containing the product from Step A (23.5 g, 77.5 mmol) was added DMSO (160 mL) followed by H2O (6.98 mL, 387 mmol) and then LiCl (16.4 g, 387 mmol). The mixture was warmed to 125° C. and stirred for 5 hours. The resulting dark mixture was then cooled to ambient temperature and diluted with EtOAc (500 mL) and washed with a saturated aqueous NaHCO3:water (1:1, 3×250 mL). The combined aqueous phase was washed with EtOAc (100 mL) and the combined organic phases were washed with brine and dried over Na2SO4, filtered and concentrated. The crude oil was purified by column chromatography (10 to 30% EtOAc/hexanes) to provide 10.0 g (56%) of the desired product as a light golden oil.

後処理

  1. temperatureThe resulting dark mixture was then cooled to ambient temperature
  2. washwashed with a saturated aqueous NaHCO3:water (1:1, 3×250 mL)
  3. washThe combined aqueous phase was washed with EtOAc (100 mL)
  4. washthe combined organic phases were washed with brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe crude oil was purified by column chromatography (10 to 30% EtOAc/hexanes)

出典と根拠

ORDレコード
ord-73bd2f72bb304bff9bc0a66298f8e098
出典データセット
uspto-grants-2015_03
特許番号
US08987251B2

反応ノート

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