Diisopropylethylamine → 3-Fluoro-5-trifluoromethylbenzyl 3-oxo-1-isopropylpentane-carboxamide

HRID 1725760ノート

反応式

HRID 1725760 の反応式
[F:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([C:10]([F:13])([F:12])[F:11])[CH:9]=1)[CH2:5]N.C([N:17](C(C)C)CC)(C)C.[CH:23]([C:26]1([C:32](Cl)=[O:33])[CH2:30][CH2:29][C:28](=[O:31])[CH2:27]1)([CH3:25])[CH3:24]>ClCCl>[F:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([C:10]([F:13])([F:12])[F:11])[CH:9]=1)[CH2:5][C:26]([CH:23]([CH3:25])[CH3:24])([C:32]([NH2:17])=[O:33])[CH2:27][C:28](=[O:31])[CH2:29][CH3:30]

参加物

5

反応物 3

HCID 81531DiisopropylethylamineHCID 27333043-Fluoro-5-(trifluoromethyl)benzylamineHCID 186143461-Isopropyl-3-oxocyclopentanoyl chloride

生成物 1

HCID 867608163-Fluoro-5-trifluoromethylbenzyl 3-oxo-1-isopropylpentane-carboxamide収率 85%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

A solution of 3-fluoro-5-trifluoromethylbenzylamine (3.07 g, 15.9 mmol) and diisopropylethylamine (2.77 mL, 15.9 mmol) in dichloromethane (60 mL) was slowly treated with 1-isopropyl-3-oxocyclopentanoyl chloride (3.0 g, 15.9 mmol) and stirred at ambient temperature overnight. The mixture was diluted with dichloromethane washed with a saturated solution of sodium bicarbonate, 2N HCl, water and brine. The organic phase was dried with anhydrous magnesium sulfate and the solvent was evaporated in vacuo to yield 6.0 g of crude product. This was further purified by column chromatography (silica gel, ethyl acetate hexane (40:60%) to yield 4.10 g (85%) of the pure product. 1H NMR (500 MHz, CDCl3): 7.32 (s, 1H), 7.23 (d, J=8.23 Hz, 1H), 7.19 (d, J=8.93 Hz, 1H), 4.52 (m, 2H), 2.79 (d, J=18.53 Hz, 1H), 2.40 to 2.18 (bm, 4H), 2.0 (m, 2H), 0.98 (d, J=6.63 Hz, 3H), 0.96 (d, 6.60 Hz, 3H).

後処理

  1. washwashed with a saturated solution of sodium bicarbonate, 2N HCl, water and brine
  2. dry with materialThe organic phase was dried with anhydrous magnesium sulfate
  3. customthe solvent was evaporated in vacuo
  4. customto yield 6.0 g of crude product
  5. customThis was further purified by column chromatography (silica gel, ethyl acetate hexane (40:60%)

出典と根拠

ORDレコード
ord-9f09b93ea2a74434a830d23ac7d2666a
出典データセット
uspto-grants-2009_02
特許番号
US07491737B2

反応ノート

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