Perchloric Acid → HCID 11616429, compound

HRID 1927542Notes

Reaction equation

HRID 1927542 reaction equation
Cl(O)(=O)(=O)=O.[CH3:6][O:7][C:8]([C:10]1[CH:11]=[CH:12][C:13]2[CH:19](O)[C:18]3[CH:21]=[CH:22][CH:23]=[CH:24][C:17]=3[CH2:16][S:15](=[O:26])(=[O:25])[C:14]=2[CH:27]=1)=[O:9].[H][H]>C(O)(=O)C.[Pd]>[CH3:6][O:7][C:8]([C:10]1[CH:11]=[CH:12][C:13]2[CH2:19][C:18]3[CH:21]=[CH:22][CH:23]=[CH:24][C:17]=3[CH2:16][S:15](=[O:25])(=[O:26])[C:14]=2[CH:27]=1)=[O:9]

Participants

6

Reactant 3

HCID 24247Perchloric AcidHCID 11681258HCID 11681258, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 11616429HCID 11616429, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Conditions

Temperature
25 °C

Procedure

Pd/C (0.015 g, 10% w/w) and catalytic amount of perchloric acid was added to a solution compound of Example 203 (0.11 g, 0.3 mmol) in acetic acid (60 ml). The reaction mixture was subjected to hydrogenation at 100 psi of hydrogen at 65° C. for 6.5 h. The reaction mixture was cooled to 25° C. and filtered through high flow bed. The filtrate was concentrated, diluted with water and extracted with ethyl acetate. The combined organic layer was washed with water, brine, concentrated and purified using flash chromatography (silica gel, ethyl acetate and pet ether) to obtain the title compound. Yield: 0.05 g (47%); 1H NMR (CDCl3): δ 3.8 (s, 2H, CH2), 3.9 (s, 3H, CH3), 4.32 (s, 2H, CH2), 7.38 (m, 5H, Ar), 8.09 (d, 1H, Ar), 8.61 (s, 1H, Ar); MS: m/e (CI+) 303 (M+1).

Workup

  1. filtrationfiltered through high flow bed
  2. concentrationThe filtrate was concentrated
  3. additiondiluted with water
  4. extractionextracted with ethyl acetate
  5. washThe combined organic layer was washed with water, brine
  6. concentrationconcentrated
  7. custompurified

Sources & evidence

ORD record
ord-a156229c921c406ba88e4b1c0deeca23
Source dataset
uspto-grants-2012_05
Patent number
US08183234B2

Reaction notes

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