Trifluoroacetic acid → 3-(4-Isopropoxy-3-methyl-benzoyl)-11-oxa-3-azaspiro[5.5]undec-9-en-8-one

HRID 1478428ノート

反応式

HRID 1478428 の反応式
[CH2:1]1[C:6]2([O:11][CH:10]=[CH:9][C:8](=[O:12])[CH2:7]2)[CH2:5][CH2:4][NH:3][CH2:2]1.FC(F)(F)C(O)=O.C(N(CC)CC)C.[CH:27]([O:30][C:31]1[CH:39]=[CH:38][C:34]([C:35](Cl)=[O:36])=[CH:33][C:32]=1[CH3:40])([CH3:29])[CH3:28]>C(Cl)Cl>[CH:27]([O:30][C:31]1[CH:39]=[CH:38][C:34]([C:35]([N:3]2[CH2:2][CH2:1][C:6]3([O:11][CH:10]=[CH:9][C:8](=[O:12])[CH2:7]3)[CH2:5][CH2:4]2)=[O:36])=[CH:33][C:32]=1[CH3:40])([CH3:29])[CH3:28]

参加物

6

反応物 4

HCID 6422Trifluoroacetic acidHCID 8471TriethylamineHCID 874026094-Isopropoxy-3-methyl-benzoyl chlorideHCID 897083431-Oxa-9-azaspiro[5.5]undec-2-en-4-one

生成物 1

HCID 897085293-(4-Isopropoxy-3-methyl-benzoyl)-11-oxa-3-azaspiro[5.5]undec-9-en-8-one

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒3 回

実験手順

To a solution of 11-oxa-3-azaspiro[5.5]undec-9-en-8-one; 2,2,2-trifluoroacetic acid (2.42 g, 8.6 mmol) in CH2Cl2 (35 mL) was added triethylamine (10.9 mL, 78.2 mmol) followed by the addition of 4-isopropoxy-3-methyl-benzoyl chloride (1.83 g, 8.60 mmol) in CH2Cl2 (5 mL) dropwise. The mixture was stirred at room temperature overnight. The mixture was diluted with CH2Cl2, washed with water, dried over MgSO4, filtered and concentrated to dryness. The crude material was purified by column chromatography (30-50% ethyl acetate-Hex) to provide 3-(4-isopropoxy-3-methyl-benzoyl)-11-oxa-3-azaspiro[5.5]undec-9-en-8-one (2.65 g) as a light yellow solid. 1H NMR (400 MHz, CDCl3) δ 7.27 (t, J=4.0 Hz, 1H), 7.25-7.17 (m, 2H), 6.81 (d, J=8.1 Hz, 1H), 5.43 (d, J=6.1 Hz, 1H), 4.56 (dd, J=12.1, 6.0 Hz, 1H), 4.43-3.61 (m, 2H), 3.33 (s, 2H), 2.55 (s, 2H), 2.20 (s, 3H), 2.13 (d, J=13.2 Hz, 2H), 1.61 (s, 2H), 1.35 (d, J=6.0 Hz, 6H). ESI-MS m/z calc. 343.18, found 344.3 (M+1)+; Retention time: 1.50 minutes (3 minute run).

後処理

  1. washwashed with water
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated to dryness
  5. customThe crude material was purified by column chromatography (30-50% ethyl acetate-Hex)

出典と根拠

ORDレコード
ord-fac1e85c8a424f6896dce7d7a0d74924
出典データセット
uspto-grants-2016_08
特許番号
US09403839B2

反応ノート

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