HCID 67235025, compound → HCID 46927579, compound

HRID 882718Notes

Reaction equation

HRID 882718 reaction equation
C([O:8][C:9]1[CH:28]=[CH:27][C:12]([O:13][C:14]2[CH:26]=[CH:25][C:17]3[NH:18][CH2:19][CH2:20][NH:21][S:22](=[O:24])(=[O:23])[C:16]=3[CH:15]=2)=[CH:11][CH:10]=1)C1C=CC=CC=1>C(O)C.Cl.O1CCOCC1.[Pd]>[O:24]=[S:22]1(=[O:23])[C:16]2[CH:15]=[C:14]([O:13][C:12]3[CH:27]=[CH:28][C:9]([OH:8])=[CH:10][CH:11]=3)[CH:26]=[CH:25][C:17]=2[NH:18][CH2:19][CH2:20][NH:21]1

Participants

6

Reactant 1

HCID 67235025HCID 67235025, compound

Product 1

HCID 46927579HCID 46927579, compound

Reagents, catalysts & solvents 4

HCID 313Hydrochloric AcidCatalystHCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 312751,4-DioxaneSolvent

Procedure

The product of Example 8 (0.76 mmol) is hydrogenated for 1 hour at atmospheric pressure in 60 ml of ethanol in the presence of 30 mg of 10% palladium-on-carbon and 2 drops of 4N HCl solution in dioxane. The catalyst is removed by filtration and the filtrate is evaporated to dryness. The residue is taken up in the hot state in ethyl acetate. The organic phase is washed with 1% NaHCO3 solution and then with saturated NaCl solution, dried (MgSO4), filtered and evaporated. The residue is triturated in a mixture of ethyl acetate/ethyl ether to yield, after filtration, the title product.

Workup

  1. customThe catalyst is removed by filtration
  2. customthe filtrate is evaporated to dryness
  3. washThe organic phase is washed with 1% NaHCO3 solution
  4. dry with materialwith saturated NaCl solution, dried (MgSO4)
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue is triturated in a mixture of ethyl acetate/ethyl ether
  8. customto yield
  9. filtrationafter filtration

Sources & evidence

ORD record
ord-ae03ca092d414c12a3832315134a07b6
Source dataset
uspto-grants-2012_08
Patent number
US08236790B2

Reaction notes

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