HCID 86633378, compound → HCID 86633377, compound

HRID 1009678Notes

Reaction equation

HRID 1009678 reaction equation
[Na:1].C([O:9][C@@H:10]1[C@@H:15]([O:16]CC2C=CC=CC=2)[C@H:14]([O:24]CC2C=CC=CC=2)[C@@H:13]([CH2:32][S:33]([OH:36])(=[O:35])=[O:34])[O:12][C@@H:11]1[O:37][CH2:38][CH2:39][CH2:40][O:41][C:42](=[O:60])[CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][CH2:54][CH2:55][CH2:56][CH2:57][CH2:58][CH3:59])C1C=CC=CC=1.[H][H]>C(O)C.ClCCl.[Pd]>[Na:1].[S:33]([CH2:32][C@H:13]1[O:12][C@H:11]([O:37][CH2:38][CH2:39][CH2:40][O:41][C:42](=[O:60])[CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][CH2:54][CH2:55][CH2:56][CH2:57][CH2:58][CH3:59])[C@H:10]([OH:9])[C@@H:15]([OH:16])[C@@H:14]1[OH:24])([OH:36])(=[O:34])=[O:35]

Participants

6

Reactant 2

HCID 86633378HCID 86633378, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 86633377HCID 86633377, compound

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of the compound (9) (28.7 g, 33.3 mmol) in ethanol (400 ml) and dichloromethane (150 ml) was added 10% palladium activated carbon (7.00 g), and the mixture was stirred at room temperature for 48 hours in a hydrogen gas atmosphere. After the sufficient progress of the reaction was confirmed, palladium activated carbon was removed by filtration, and the filtrate was concentrated under reduced pressure. The obtained residue was purified with silica gel chromatography (dichloromethane-methanol, 10:1→5:1→3:1→2:1→1:1), and precipitated from 98% heated ethanol to obtain the title compound (10) in the form of a colorless powder {15.6 g (26.4 mmol), 79.4%}.

Workup

  1. custompalladium activated carbon was removed by filtration
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customThe obtained residue was purified with silica gel chromatography (dichloromethane-methanol, 10:1→5:1→3:1→2:1→1:1)
  4. customprecipitated from 98%
  5. temperatureheated ethanol

Sources & evidence

ORD record
ord-30f3ba303eec4e5e8dd2cf372180b6f7
Source dataset
uspto-grants-2011_07
Patent number
US07973145B2

Reaction notes

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