HCID 19754877, compound → HCID 19754890, compound

HRID 1588910Notes

Reaction equation

HRID 1588910 reaction equation
[CH:1]1([N:7]([CH:30]([CH3:32])[CH3:31])[C:8](=[O:29])[C:9]2[CH:14]=[CH:13][C:12]([CH:15](O)[C:16]3[CH:21]=[C:20]([O:22][CH3:23])[C:19]([O:24][CH3:25])=[C:18]([O:26][CH3:27])[CH:17]=3)=[CH:11][CH:10]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1>C(O)C.S(=O)(=O)(O)O.[Pd].C(OCC)(=O)C>[CH:1]1([N:7]([CH:30]([CH3:32])[CH3:31])[C:8](=[O:29])[C:9]2[CH:14]=[CH:13][C:12]([CH2:15][C:16]3[CH:21]=[C:20]([O:22][CH3:23])[C:19]([O:24][CH3:25])=[C:18]([O:26][CH3:27])[CH:17]=3)=[CH:11][CH:10]=2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

6

Reactant 1

HCID 19754877HCID 19754877, compound

Product 1

HCID 19754890HCID 19754890, compound

Reagents, catalysts & solvents 4

HCID 1118Sulfuric AcidCatalystHCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

The compound prepared in Example 14 (800 mg, 1.81 mmol) in ethyl alcohol (20 mL) containing concentrated sulfuric acid (4 drops) was hydrogenated at 60 psi and room temperature using 5% Pd/C as catalyst. The catalyst was filtered and the filtrate concentrated in vacuo to give the crude product as an oil. The crude product was dissolved in ethyl acetate and washed twice with aqueous NaHCO3 solution and then with saturated aqueous NaCl solution. After drying (Na2SO4), the organic layer was filtered and concentrated in vacuo to give the title compound.

Workup

  1. customwas hydrogenated at 60 psi and room temperature
  2. filtrationThe catalyst was filtered
  3. concentrationthe filtrate concentrated in vacuo
  4. customto give the crude product as an oil
  5. washwashed twice with aqueous NaHCO3 solution
  6. dry with materialAfter drying (Na2SO4)
  7. filtrationthe organic layer was filtered
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-3c609271f8684570b01610051d46cf62
Source dataset
uspto-grants-1993_06
Patent number
US05223539

Reaction notes

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