Perchloric Acid → HCID 11616429, compound

HRID 1695299Notes

Reaction equation

HRID 1695299 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-0fe91d85d3b14139b77a3d4cba11bf30
Source dataset
uspto-grants-2012_04
Patent number
US08163730B2

Reaction notes

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