Potassium Formate → HCID 44301370, compound

HRID 482215Notes

Reaction equation

HRID 482215 reaction equation
[N:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[NH:3][C:2]=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.C([O-])=O.[K+]>C(O)C.O.[Pd]>[N:3]1[C:4]2[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=2[NH:1][C:2]=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

Participants

6

Reactant 2

HCID 2735122Potassium FormateHCID 69704240HCID 69704240, compound

Product 1

HCID 44301370HCID 44301370, compoundYield 76.5%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a solution of the product of Example 22 (669 mg, 1.52 mmol) in 20 mL of absolute ethanol under a N2 blanket was added 10% Pd/C (335 mg) followed by a solution of potassium formate (461 mg, 5.48 mmol) in 0.5 mL of water. After 1 h, the reaction mixture was filtered through a pad of celite and concentrated by rotary evaporation. The solid residue was partioned between ethyl acetate and water and the organic layer was washed with brine and dried over Na2SO4. Solvent was removed by rotary evaporation and the residue was purified by silica gel chromatography (40% hexanes in ethyl acetate) to afford 478 mg (76.5%) of the title compound. MS (FD+)=411. IR: 1623, 1543, 1486 cm-1. 1H NMR (CDCl3, 300 MHz) δ 1.29 (d, 3, J=7); 2.82 (dd, 1, J=10, 14); 3.02 (dd, 1, J=4, 14); 3.96 (s, 2); 5.46 (m, 1); 6.00 (d, 2, J=8); 6.71 (m, 4); 7.08 (m, 2); 7.30 (s, 1); 7.52 (m, 3); 9.00 (s, 1).

Workup

  1. filtrationthe reaction mixture was filtered through a pad of celite
  2. concentrationconcentrated by rotary evaporation
  3. washthe organic layer was washed with brine
  4. dry with materialdried over Na2SO4
  5. customSolvent was removed by rotary evaporation
  6. customthe residue was purified by silica gel chromatography (40% hexanes in ethyl acetate)

Sources & evidence

ORD record
ord-95d3bfe15ca04ec283c1c45dcd67c337
Source dataset
uspto-grants-1998_08
Patent number
US05795886

Reaction notes

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