HCID 19754891, compound → HCID 19754895, compound

HRID 1588935Notes

Reaction equation

HRID 1588935 reaction equation
[CH:1]1([N:7]([CH:31]([CH3:33])[CH3:32])[C:8](=[O:30])[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)=[C:11]([CH3:29])[CH:10]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1>CCO.S(=O)(=O)(O)O.[Pd].C(OCC)(=O)C>[CH:1]1([N:7]([CH:31]([CH3:33])[CH3:32])[C:8](=[O:30])[C:9]2[CH:14]=[CH:13][C:12]([CH2:15][C:16]3[CH:17]=[C:18]([O:26][CH3:27])[C:19]([O:24][CH3:25])=[C:20]([O:22][CH3:23])[CH:21]=3)=[C:11]([CH3:29])[CH:10]=2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

6

Reactant 1

HCID 19754891HCID 19754891, compound

Product 1

HCID 19754895HCID 19754895, compound

Reagents, catalysts & solvents 4

HCID 1118Sulfuric AcidCatalystHCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

The compound of Example 47 (800 mg, 1.81 mmol) in EtOH (20 mL) containing concentrated sulfuric acid (4 drops) is hydrogenated at 60 psi and room temperature using 5% Pd/C as catalyst. The catalyst is filtered and the filtrate concentrated in vacuo to give the crude product. The crude product is dissolved in ethyl acetate and washed twice with aqueous NaHO3 solution and then with saturated aqueous NaCl solution. After drying (Na2SO4) the organic layer is filtered and concentrated in vacuo. Purification to give the title compound is carried out by chromatography of the residue on silica gel using mixtures of ethyl acetate and hexane as the eluents.

Workup

  1. customis hydrogenated at 60 psi and room temperature
  2. filtrationThe catalyst is filtered
  3. concentrationthe filtrate concentrated in vacuo
  4. customto give the crude product
  5. washwashed twice with aqueous NaHO3 solution
  6. dry with materialAfter drying (Na2SO4) the organic layer
  7. filtrationis filtered
  8. concentrationconcentrated in vacuo
  9. customPurification

Sources & evidence

ORD record
ord-12ef888ae3f64d01b0e0f1df7eb04043
Source dataset
uspto-grants-1993_06
Patent number
US05223539

Reaction notes

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