Ethyl Acetate → HCID 68885701, compound

HRID 2109293Notes

Reaction equation

HRID 2109293 reaction equation
[CH3:1][O:2][C:3]1[C:8]([N+:9]([O-])=O)=[CH:7][C:6]([C:12]([CH3:19])([CH3:18])[CH2:13][O:14][C:15](=[O:17])[CH3:16])=[CH:5][C:4]=1[N+:20]([O-])=O.C(OCC)(=O)C.C([O-])=O.[NH4+]>CO.[Pd]>[NH2:9][C:8]1[CH:7]=[C:6]([C:12]([CH3:19])([CH3:18])[CH2:13][O:14][C:15](=[O:17])[CH3:16])[CH:5]=[C:4]([NH2:20])[C:3]=1[O:2][CH3:1]

Participants

6

Reactant 3

HCID 8857Ethyl AcetateHCID 2723923Ammonium formateHCID 86604276HCID 86604276, compound

Product 1

HCID 68885701HCID 68885701, compoundYield 99.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Conditions

Temperature
40 °C

Procedure

Acetic acid 2-(4-methoxy-3,5-dinitro-phenyl)-2-methyl-propyl ester (625 mg, 2.00 mmol) was dissolved in 10 mL MeOH. Ethyl acetate (10 mL), ammonium formate (1.26 g, 20.0 mmol), and Pd/C (56 mg) were added and the mixture was heated to 40° C. overnight. The mixture was then filtered through celite and partitioned between sat'd NaHCO3 and EtOAc. The EtOAc extract was washed with brine. The washes were extracted once more with EtOAc. The extracts were combined, dried with Na2SO4, filtered, and concentrated to provide 500 mg of acetic acid 2-(3,5-diamino-4-methoxy-phenyl)-2-methyl-propyl ester.

Workup

  1. filtrationThe mixture was then filtered through celite
  2. custompartitioned between sat'd NaHCO3 and EtOAc
  3. extractionThe EtOAc extract
  4. washwas washed with brine
  5. extractionThe washes were extracted once more with EtOAc
  6. dry with materialdried with Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-e60abb9d888f4481b2bfed4ce6bb89cf
Source dataset
uspto-grants-2009_04
Patent number
US07514458B2

Reaction notes

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