Water → 2-acetamido-N-tert-butyl-2-(4-(4-chlorophenyl)cyclohexyl)hex-5-enamide

HRID 579598

反応式

HRID 579598 の反応式
[C:1]([N+:5]#[C-:6])([CH3:4])([CH3:3])[CH3:2].[Cl:7][C:8]1[CH:13]=[CH:12][C:11]([CH:14]2[CH2:19][CH2:18][CH:17]([C:20](=O)[CH2:21][CH2:22][CH:23]=[CH2:24])[CH2:16][CH2:15]2)=[CH:10][CH:9]=1.[C:26]([O-:29])(=O)[CH3:27].[NH4+:30].[OH2:31]>FC(F)(F)CO>[C:26]([NH:30][C:20]([CH:17]1[CH2:18][CH2:19][CH:14]([C:11]2[CH:12]=[CH:13][C:8]([Cl:7])=[CH:9][CH:10]=2)[CH2:15][CH2:16]1)([CH2:21][CH2:22][CH:23]=[CH2:24])[C:6]([NH:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:31])(=[O:29])[CH3:27]

参加物

6

反応物 4

HCID 962WaterHCID 23577Tert-Butyl isocyanideHCID 517165Ammonium AcetateHCID 668327641-[4-(4-Chlorophenyl)-cyclohexyl]pent-4-en-1-one

生成物 1

HCID 668336582-acetamido-N-tert-butyl-2-(4-(4-chlorophenyl)cyclohexyl)hex-5-enamide収率 77%

試薬・触媒・溶媒 1

HCID 64092,2,2-Trifluoroethanol溶媒

実験手順

tert-Butyl isocyanide (301 mg, 0.41 mL, 3.6 mmol) was added to a stirred slurry of 1-[4-(4-chlorophenyl)-cyclohexyl]pent-4-en-1-one (800 mg, 2.9 mmol) and ammonium acetate (671 mg, 8.7 mmol) in 2,2,2-trifluoroethanol (0.4 mL). After stirring at room temperature for 8 days, the reaction mixture was poured into water and extracted with ethyl acetate (3×). The combined organic phase was washed with saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate, filtered and concentrated in vacuo. Purification by flash column chromatography (silica gel, 10-50% ethyl acetate in heptane) gave 2-acetamido-N-tert-butyl-2-(4-(4-chlorophenyl)cyclohexyl)hex-5-enamide as a colorless oil (940 mg, 77%); 1H NMR (CDCl3, 300 MHz) δ 7.24 (m, 2H), 7.15 (m, 2H), 7.04 (br s, NH, 1H), 5.80 (m, 1H), 5.544 (br s, NH, 1H), 4.97 (m, 2H), 3.04 (ddd, J1=14 Hz, J2=11.5 Hz, J3=5.0 Hz, 1H), 2.38 (tt, J1=12 Hz, J2=2 Hz, 1H), 2.28 (tt, J1=12 Hz, J2=2 Hz, 1H), 2.03 (s, 3H), 1.68-1.95 (m, 5H), 1.42-1.61 (m, 4H), 1.41 (s, 9H), 1.26 (m, 1H) and 1.12 (m, 1H); MS (+CI): m/z for C24H35ClN2O2: expected 418.2. found 419.2 (M+H)+.

後処理

  1. extractionextracted with ethyl acetate (3×)
  2. washThe combined organic phase was washed with saturated aqueous sodium chloride
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customPurification by flash column chromatography (silica gel, 10-50% ethyl acetate in heptane)

出典と根拠

ORDレコード
ord-c155a9d4a2f54fc7b4545d6b462b08ee
出典データセット
uspto-grants-2015_05
特許番号
US09040703B2

関連ノート

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