Ammonium formate → HCID 59909743, compound

HRID 1279897Notes

Reaction equation

HRID 1279897 reaction equation
[CH:1]1(/[CH:5]=[CH:6]\[CH2:7][C@@H:8]([C:17]2[O:18][CH:19]=[C:20]([C:22]([N:24]([CH3:26])[CH3:25])=[O:23])[N:21]=2)[CH2:9][C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH2:4][CH2:3][CH2:2]1.C([O-])=O.[NH4+]>C(O)C.[OH-].[Pd+2].[OH-]>[CH:1]1([CH2:5][CH2:6][CH2:7][C@@H:8]([C:17]2[O:18][CH:19]=[C:20]([C:22]([N:24]([CH3:26])[CH3:25])=[O:23])[N:21]=2)[CH2:9][C:10]([O:12][C:13]([CH3:15])([CH3:16])[CH3:14])=[O:11])[CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 59909738HCID 59909738, compound

Product 1

HCID 59909743HCID 59909743, compoundYield 93.7%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 702EthanolSolvent

Procedure

A solution of tert-butyl (3R,5Z)-6-cyclobutyl-3-{4-[(dimethylamino)carbonyl]-1,3-oxazol-2-yl}-5-hexenoate (Preparation 119) (260 mg, 0.72 mmol) in ethanol (15 ml) was treated with palladium hydroxide (250 mg) followed by ammonium formate (500 mg) and the mixture was stirred at reflux for 3 hours. The reaction mixture was allowed to cool to room temperature and was filtered through arbacel. The solvent was removed under reduced pressure. The residue was dissolved in ethyl acetate and washed with water and brine, dried over anhydrous sodium sulphate and filtered. The solvent was removed under reduced pressure to afford the title compound as a colourless oil (246 mg).

Workup

  1. temperatureat reflux for 3 hours
  2. filtrationwas filtered through arbacel
  3. customThe solvent was removed under reduced pressure
  4. dissolutionThe residue was dissolved in ethyl acetate
  5. washwashed with water and brine
  6. dry with materialdried over anhydrous sodium sulphate
  7. filtrationfiltered
  8. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-674ef5946a5f45d3b75275f86bdcd757
Source dataset
uspto-grants-2002_09
Patent number
US06448278B2

Reaction notes

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