Potassium Formate → HCID 69703307, compound

HRID 482216Notes

Reaction equation

HRID 482216 reaction equation
[CH3:1][O:2][C:3]([C:5]1[S:6][CH:7]=[CH:8][C:9]=1[N:10]1[C@H:16]([CH3:17])[CH2:15][C:14]2[CH:18]=[C:19]3[O:24][CH2:23][O:22][C:20]3=[CH:21][C:13]=2[C:12]([C:25]2[CH:30]=[CH:29][C:28]([N+:31]([O-])=O)=[CH:27][CH:26]=2)=[N:11]1)=[O:4].C([O-])=O.[K+]>C(O)C.CC(C)=O.O.[Pd]>[CH3:1][O:2][C:3]([C:5]1[S:6][CH:7]=[CH:8][C:9]=1[N:10]1[C@H:16]([CH3:17])[CH2:15][C:14]2[CH:18]=[C:19]3[O:24][CH2:23][O:22][C:20]3=[CH:21][C:13]=2[C:12]([C:25]2[CH:26]=[CH:27][C:28]([NH2:31])=[CH:29][CH:30]=2)=[N:11]1)=[O:4]

Participants

7

Reactant 2

HCID 2735122Potassium FormateHCID 86753029HCID 86753029, compound

Product 1

HCID 69703307HCID 69703307, compoundYield 91.6%

Reagents, catalysts & solvents 4

HCID 23938PalladiumCatalystHCID 180AcetoneSolventHCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a solution of the product of Example 24 (794 mg, 1.71 mmol) in 16 mL of absolute ethanol and 3 mL of acetone under N2 was added 10% Pd/C (400 mg) followed by a solution of potassium formate (513 mg, 6.10 mmol) in 1 mL of H2O. After 50 min, the mixture was filtered through a pad of celite and concentrated by rotary evaporation. The residue was partitioned between ethyl acetate and water and the organic layer was washed with brine and dried over Na2SO4. The solvent was removed by rotary evaporation and the residue was purified by silica gel chromatography (1:1 ethyl acetate hexanes) to afford 682 mg of the desired final product.

Workup

  1. filtrationthe mixture was filtered through a pad of celite
  2. concentrationconcentrated by rotary evaporation
  3. customThe residue was partitioned between ethyl acetate and water
  4. washthe organic layer was washed with brine
  5. dry with materialdried over Na2SO4
  6. customThe solvent was removed by rotary evaporation
  7. customthe residue was purified by silica gel chromatography (1:1 ethyl acetate hexanes)

Sources & evidence

ORD record
ord-82c198535dd0486d918241fa14fc2856
Source dataset
uspto-grants-1998_08
Patent number
US05795886

Reaction notes

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