Sodium Acetate → HCID 66879934, compound

HRID 1893547Notes

Reaction equation

HRID 1893547 reaction equation
[CH2:1]([O:3][C:4](=[O:27])[CH2:5][N:6]([CH2:21][C:22]([O:24][CH2:25][CH3:26])=[O:23])[C:7]1[CH:12]=[C:11]([C:13]2[CH:18]=[C:17](Cl)[N:16]=[CH:15][N:14]=2)[CH:10]=[CH:9][C:8]=1[CH3:20])[CH3:2].C([O-])(=O)C.[Na+]>C(O)C.O1CCCC1.[C].[Pd]>[CH2:25]([O:24][C:22](=[O:23])[CH2:21][N:6]([CH2:5][C:4]([O:3][CH2:1][CH3:2])=[O:27])[C:7]1[CH:12]=[C:11]([C:13]2[CH:18]=[CH:17][N:16]=[CH:15][N:14]=2)[CH:10]=[CH:9][C:8]=1[CH3:20])[CH3:26]

Participants

6

Reactant 2

HCID 517045Sodium AcetateHCID 86650782HCID 86650782, compound

Product 1

HCID 66879934HCID 66879934, compoundYield 73.2%

Reagents, catalysts & solvents 3

HCID 178418390HCID 178418390, compoundCatalystHCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

The compound (696 mg, 1.78 mmol) obtained in step B was dissolved in a ethanol (25 ml)-tetrahydrofuran (2 ml) mixed solvent. Then, sodium acetate (164 mg, 2.00 mmol) and 10% palladium carbon (containing water) (0.68 g) were added, and the mixture was stirred at room temperature for 5 hr under a hydrogen atmosphere. The insoluble material was filtered off through celite, and the solution was concentrated under reduced pressure. The obtained oil was purified by silica gel column chromatography (ethyl acetate-hexane) to give the title compound (466 mg, yield 73%) as a colorless oil.

Workup

  1. additionmixed solvent
  2. filtrationThe insoluble material was filtered off through celite
  3. concentrationthe solution was concentrated under reduced pressure
  4. customThe obtained oil was purified by silica gel column chromatography (ethyl acetate-hexane)

Sources & evidence

ORD record
ord-396c8ba2170e4212b2898823c1b31b2a
Source dataset
uspto-grants-2013_08
Patent number
US08513235B2

Reaction notes

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