Perchloric Acid → HCID 11616429, compound

HRID 2425114Notes

Reaction equation

HRID 2425114 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 of compound of Example 40 (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 60-80° C.) to obtain the title compound. Yield: 0.05 g (47%); 1H NMR (CDCl3, 300 MHz): δ 3.90 (s, 3H, OCH3), 4.32 (s, 2H, CH2), 5.21 (s, 2H, CH2) 7.38 (m, 5H, Ar), 8.09 (d, 1H, Ar), 8.61 (s, 1H, Ar); MS: m/e (Cl) 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
  8. customflash chromatography (silica gel, ethyl acetate and pet. ether 60-80° C.)

Sources & evidence

ORD record
ord-bea402ea57fb4168bd7a040cc89840ce
Source dataset
uspto-grants-2011_06
Patent number
US07964631B2

Reaction notes

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