Water → Benzyl 4-(aminocarbonyl)-3-(cyclohexylamino)benzoate

HRID 906147노트

반응식

HRID 906147 반응식
[C:1]([C:3]1[CH:18]=[CH:17][C:6]([C:7]([O:9][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[O:8])=[CH:5][C:4]=1[NH:19][CH:20]1[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]1)#[N:2].C(=O)([O-])[O-:27].[K+].[K+].O>CS(C)=O.OO.C(OCC)(=O)C>[NH2:2][C:1]([C:3]1[CH:18]=[CH:17][C:6]([C:7]([O:9][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[O:8])=[CH:5][C:4]=1[NH:19][CH:20]1[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]1)=[O:27]

참가 물질

7

반응물 3

HCID 962WaterHCID 11430Potassium CarbonateHCID 67405391Benzyl 4-cyano-3-(cyclohexylamino)benzoate

생성물 1

HCID 67403240Benzyl 4-(aminocarbonyl)-3-(cyclohexylamino)benzoate수율 64.6%

시약·촉매·용매 3

HCID 784Hydrogen Peroxide촉매HCID 679Dimethyl Sulfoxide용매HCID 8857Ethyl Acetate용매

실험 절차

To a solution of benzyl 4-cyano-3-(cyclohexylamino)benzoate (66.2 mg, 0.198 mmol) in DMSO (2 mL) was added potassium carbonate (27.4 mg, 0.198 mmol) followed by 30% aqueous hydrogen peroxide (5 drops). The mixture was stirred at room temperature for 45 min, and was then diluted with ethyl acetate. Water was added and then the layers were separated. The aqueous phase was then extracted with ethyl acetate. The combined organic extracts were dried over magnesium sulfate, filtered, and concentrated. The residue was purified by column chromatography (40% ethyl acetate in hexanes) to provide benzyl 4-(aminocarbonyl)-3-(cyclohexylamino)benzoate (45.0 mg, 0.128 mmol, 64% yield) as a yellow film. 1H NMR (400 MHz, CDCl3): 7.81 (d, 1H), 7.46-7.32 (m, 7H), 7.16 (dd, 1H), 5.77 (br s, 2H), 5.36 (s, 2H), 3.48-3.38 (m, 1H), 2.05-1.98 (m, 2H), 1.80-1.72 (m, 2H), 1.66-1.59 (m, 1H), 1.45-1.23 (m, 4H); MS (EI) for C21H24N2O3: 353 (MH+).

후처리

  1. customthe layers were separated
  2. extractionThe aqueous phase was then extracted with ethyl acetate
  3. dry with materialThe combined organic extracts were dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified by column chromatography (40% ethyl acetate in hexanes)

출처 및 근거

ORD 기록
ord-b7bccb50a8d44d98a42e3a25f7f086e7
출처 데이터셋
uspto-grants-2011_09
특허 번호
US08012956B2

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