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

HRID 1478428노트

반응식

HRID 1478428 반응식
[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]

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매3회

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-fac1e85c8a424f6896dce7d7a0d74924
출처 데이터셋
uspto-grants-2016_08
특허 번호
US09403839B2

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