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

HRID 906147ノート

反応式

HRID 906147 の反応式
[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]

参加物

7

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 784Hydrogen Peroxide触媒HCID 679Dimethyl Sulfoxide溶媒HCID 8857Ethyl Acetate溶媒

実験手順

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+).

後処理

  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)

出典と根拠

ORDレコード
ord-b7bccb50a8d44d98a42e3a25f7f086e7
出典データセット
uspto-grants-2011_09
特許番号
US08012956B2

反応ノート

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