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

HRID 906147Notes

Reaction equation

HRID 906147 reaction equation
[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]

Participants

7

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 3

HCID 784Hydrogen PeroxideCatalystHCID 679Dimethyl SulfoxideSolventHCID 8857Ethyl AcetateSolvent

Procedure

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+).

Workup

  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)

Sources & evidence

ORD record
ord-b7bccb50a8d44d98a42e3a25f7f086e7
Source dataset
uspto-grants-2011_09
Patent number
US08012956B2

Reaction notes

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