HCID 20304552, compound → HCID 20304538, compound

HRID 236963Notes

Reaction equation

HRID 236963 reaction equation
[CH2:1]([O:4][C:5]1[C:18]2[C:17](=[O:19])[CH:16]=[C:15]([C:20]([OH:22])=[O:21])[O:14][C:13]=2[C:12]([CH2:23][CH2:24][CH3:25])=[C:11]2[C:6]=1[CH2:7][CH2:8][CH2:9][CH2:10]2)[CH:2]=[CH2:3]>C(O)C.[Pd]>[O:19]=[C:17]1[CH:16]=[C:15]([C:20]([OH:22])=[O:21])[O:14][C:13]2[C:12]([CH2:23][CH2:24][CH3:25])=[C:11]3[C:6](=[C:5]([O:4][CH2:1][CH2:2][CH3:3])[C:18]1=2)[CH2:7][CH2:8][CH2:9][CH2:10]3

Participants

4

Reactant 1

HCID 20304552HCID 20304552, compound

Product 1

HCID 20304538HCID 20304538, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of the product of Example 23 (1.4 g) in ethanol (25 ml) was treated with a 5% palladium on charcoal catalyst (50 mg) and hydrogenated at 45 psi/room temperature for 5 hours. Catalyst was filtered off and the ethanolic filtrate was evaporated to low bulk, treated with sodium bicarbonate (0.8 g) and water (30 ml), and heated under reflux for 1 hour. The solution was evaporated, diluted with water and filtered and the filtrate was acidified. The precipitated acid was filtered off, washed with water, dried and the title compound recovered as a pale yellow powder (1.4 g), mp 208° (decomp).

Workup

  1. filtrationCatalyst was filtered off
  2. customthe ethanolic filtrate was evaporated to low bulk
  3. additiontreated with sodium bicarbonate (0.8 g) and water (30 ml)
  4. temperatureheated
  5. temperatureunder reflux for 1 hour
  6. customThe solution was evaporated
  7. additiondiluted with water
  8. filtrationfiltered
  9. filtrationThe precipitated acid was filtered off
  10. washwashed with water
  11. customdried
  12. customthe title compound recovered as a pale yellow powder (1.4 g), mp 208° (decomp)

Sources & evidence

ORD record
ord-b8d5a4dfabe44092bedf3cf03d622121
Source dataset
uspto-grants-1979_06
Patent number
US04159273

Reaction notes

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