Ammonium formate → HCID 69103685, compound

HRID 2220395Notes

Reaction equation

HRID 2220395 reaction equation
C(OC([NH:11][C:12]([CH3:35])([CH3:34])[CH2:13][C:14]1[CH:19]=[CH:18][C:17]([C:20]2[CH:25]=[CH:24][C:23]([C:26]([O:28][CH3:29])=[O:27])=[C:22]([CH2:30][CH:31]([CH3:33])[CH3:32])[CH:21]=2)=[CH:16][CH:15]=1)=O)C1C=CC=CC=1.C([O-])=O.[NH4+]>[Pd].CO.O>[NH2:11][C:12]([CH3:34])([CH3:35])[CH2:13][C:14]1[CH:19]=[CH:18][C:17]([C:20]2[CH:25]=[CH:24][C:23]([C:26]([O:28][CH3:29])=[O:27])=[C:22]([CH2:30][CH:31]([CH3:32])[CH3:33])[CH:21]=2)=[CH:16][CH:15]=1

Participants

6

Reactant 2

HCID 2723923Ammonium formateHCID 69102817HCID 69102817, compound

Product 1

HCID 69103685HCID 69103685, compoundYield 91%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 962WaterSolvent

Procedure

The mixture of methyl 4′-[2-[[(benzyloxy)carbonyl]-amino]-2-methylpropyl]-3-isobutyl-4-biphenylcarboxylate (570 mg), ammonium formate (351 mg) and palladium on carbon powder (400 mg) in methanol (10 ml) and water (1.0 ml) was refluxed for 3 hours. The catalyst was filtered off, and the filtrate was diluted with chloroform-methanol (19:1). The organic layer was washed with saturated aqueous sodium bicarbonate solution and brine, dried over magnesium sulfate, and evaporated to give methyl 4′-(2-amino-2-methylpropyl)-3-isobutyl-4-biphenylcarboxylate (372 mg).

Workup

  1. temperaturewas refluxed for 3 hours
  2. filtrationThe catalyst was filtered off
  3. additionthe filtrate was diluted with chloroform-methanol (19:1)
  4. washThe organic layer was washed with saturated aqueous sodium bicarbonate solution and brine
  5. dry with materialdried over magnesium sulfate
  6. customevaporated

Sources & evidence

ORD record
ord-fdb0f85d709a4b599fb1955364fdc570
Source dataset
uspto-grants-2008_08
Patent number
US07417060B2

Reaction notes

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