HCID 19754873, compound → HCID 19754879, compound

HRID 1588933Notes

Reaction equation

HRID 1588933 reaction equation
[CH:1]1([N:7]([CH:32]([CH3:34])[CH3:33])[C:8](=[O:31])[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]([O:29][CH3:30])[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:32]([CH3:34])[CH3:33])[C:8](=[O:31])[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]([O:29][CH3:30])[CH:10]=2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

6

Reactant 1

HCID 19754873HCID 19754873, compound

Product 1

HCID 19754879HCID 19754879, compound

Reagents, catalysts & solvents 4

HCID 1118Sulfuric AcidCatalystHCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

The compound of Example 45 (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-e6d17f0a3da042c7a6255b8d61483c8d
Source dataset
uspto-grants-1993_06
Patent number
US05223539

Reaction notes

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