Ammonium formate → HCID 69059080, compound

HRID 1823105Notes

Reaction equation

HRID 1823105 reaction equation
[C:1]([O:5][C:6]([N:8]([CH2:27][C@@H:28]([C:30]1[CH:31]=[N:32][C:33](Cl)=[CH:34][CH:35]=1)[OH:29])[CH2:9][CH2:10][CH2:11][C:12]1[CH:17]=[CH:16][C:15]([C:18]2[CH:23]=[CH:22][C:21]([C:24]([OH:26])=[O:25])=[CH:20][CH:19]=2)=[CH:14][CH:13]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C([O-])=O.[NH4+]>[Pd].CO.O>[C:1]([O:5][C:6]([N:8]([CH2:27][C@H:28]([OH:29])[C:30]1[CH:31]=[N:32][CH:33]=[CH:34][CH:35]=1)[CH2:9][CH2:10][CH2:11][C:12]1[CH:13]=[CH:14][C:15]([C:18]2[CH:23]=[CH:22][C:21]([C:24]([OH:26])=[O:25])=[CH:20][CH:19]=2)=[CH:16][CH:17]=1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 2

HCID 2723923Ammonium formateHCID 86590691HCID 86590691, compound

Product 1

HCID 69059080HCID 69059080, compoundYield 96.5%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 962WaterSolvent

Procedure

4′-[3-[(tert-Butoxycarbonyl)[(2R)-2-(6-chloro-3-pyridyl)-2-hydroxyethyl]amino]propyl]-1,1′-biphenyl-4-carboxylic acid (100 mg), ammonium formate (50 mg) and palladium on carbon powder (30 mg) in methanol (5 ml) and water (1.0 ml) was refluxed for 30 minutes. The reaction mixture was filtrated and poured into water and extracted with ethyl acetate. The organic layer was washed with brine, dried over magnesium sulfate, and evaporated in vacuo. A mixture of the residue was chromatographed (chloroform-methanol) over silica gel to give 4′-[3-[(tert-butoxycarbonyl)[(2R)-2-hydroxy-2-(3-pyridyl)ethyl]amino]-propyl]-1,1′-biphenyl-4-carboxylic acid (90 mg) as a colorless foam.

Workup

  1. filtrationThe reaction mixture was filtrated
  2. additionpoured into water
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with brine
  5. dry with materialdried over magnesium sulfate
  6. customevaporated in vacuo
  7. additionA mixture of the residue
  8. customwas chromatographed (chloroform-methanol) over silica gel

Sources & evidence

ORD record
ord-115e952d47c34a6992d02b49ff2e0d5f
Source dataset
uspto-grants-2006_05
Patent number
US07037938B2

Reaction notes

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