HCID 67282364, compound → HCID 67281942, compound

HRID 1616176Notes

Reaction equation

HRID 1616176 reaction equation
[N+:1]([C:4]1[CH:13]=[CH:12][C:7]([C:8]([O:10][CH3:11])=[O:9])=[CH:6][C:5]=1[C:14](=[O:25])[NH:15][C:16]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)([CH3:18])[CH3:17])([O-])=O>CO.C(OCC)(=O)C.[Pd]>[NH2:1][C:4]1[CH:13]=[CH:12][C:7]([C:8]([O:10][CH3:11])=[O:9])=[CH:6][C:5]=1[C:14](=[O:25])[NH:15][C:16]([C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1)([CH3:18])[CH3:17]

Participants

5

Reactant 1

HCID 67282364HCID 67282364, compound

Product 1

HCID 67281942HCID 67281942, compoundYield 100.6%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of methyl 4-nitro-3-[(2-phenylpropan-2-yl)carbamoyl]benzoate (0.12 g, 0.35 mmol) in methanol (2.5 mL) and ethyl acetate (2.5 mL) was added 10% palladium on carbon (12 mg). The mixture was purged with H2 gas (3×) and stirred under an atmosphere of H2 for 5 h. The reaction mixture was then filtered through Celite, washed with MeOH and concentrated. The residue was purified by flash silica gel chromatography (50% to 100% EtOAc/hexanes) to afford methyl 4-amino-3-[(2-phenylpropan-2-yl)carbamoyl]benzoate (0.11 g, 99%). LC-MS: (FA) ES+ 313.

Workup

  1. customThe mixture was purged with H2 gas (3×)
  2. filtrationThe reaction mixture was then filtered through Celite
  3. washwashed with MeOH
  4. concentrationconcentrated
  5. customThe residue was purified by flash silica gel chromatography (50% to 100% EtOAc/hexanes)

Sources & evidence

ORD record
ord-bec54c875a4e4f7b994abe95b22c81f4
Source dataset
uspto-grants-2014_07
Patent number
US08765773B2

Reaction notes

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