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

HRID 1725760노트

반응식

HRID 1725760 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

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).

후처리

  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%)

출처 및 근거

ORD 기록
ord-9f09b93ea2a74434a830d23ac7d2666a
출처 데이터셋
uspto-grants-2009_02
특허 번호
US07491737B2

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