HCID 54309971, compound → HCID 19966220, compound

HRID 977845Notes

Reaction equation

HRID 977845 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([CH:11]=[C:12]([CH2:22][O:23]CC2C=CC=CC=2)[CH2:13][CH2:14][CH2:15][CH:16]2[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]2)=[CH:7][C:6]=1[NH:31][C:32](=[O:48])[CH2:33][CH:34]1[C:47]2[CH:46]=[CH:45][CH:44]=[CH:43][C:42]=2[O:41][C:40]2[C:35]1=[CH:36][CH:37]=[CH:38][CH:39]=2)([CH3:4])([CH3:3])[CH3:2].[H][H]>C(O)C.[Pd]>[C:1]([C:5]1[CH:10]=[CH:9][C:8]([CH2:11][CH:12]([CH2:22][OH:23])[CH2:13][CH2:14][CH2:15][CH:16]2[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21]2)=[CH:7][C:6]=1[NH:31][C:32](=[O:48])[CH2:33][CH:34]1[C:47]2[CH:46]=[CH:45][CH:44]=[CH:43][C:42]=2[O:41][C:40]2[C:35]1=[CH:36][CH:37]=[CH:38][CH:39]=2)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 54309971HCID 54309971, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 19966220HCID 19966220, compoundYield 93.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of 1.54 g (2.30 mmol) of N-[2-t-butyl-5-(5-cyclohexyl-2-benzyloxymethyl-1-pentenyl)phenyl]-2-(9H-xanthen-9-yl)acetamide (prepared as described in Example 208) in 15 ml of ethanol was vigorously stirred in a stream of hydrogen in the presence of 1.54 g of 10% w/w palladium-on-charcoal at room temperature for 4 hours and 20 minutes and then at 40° C. for 2 hours. At the end of this time, the reaction mixture was filtered, and the filtrate was concentrated by distillation under reduced pressure. The concentrate was purified by column chromatography through 75 g of silica gel, using a 2:3 by volume mixture of ethyl acetate and hexane as the eluent. Fractions containing the desired compound together with a small amount of impurities were combined and concentrated by distillation under reduced pressure. The concentrate was again purified by column chromatography under the same conditions as above, to give 1.19 g (yield 90%) of the title compound as a foam-like material.

Workup

  1. filtrationAt the end of this time, the reaction mixture was filtered
  2. concentrationthe filtrate was concentrated by distillation under reduced pressure
  3. customThe concentrate was purified by column chromatography through 75 g of silica gel
  4. additionby volume mixture of ethyl acetate and hexane as the eluent
  5. additionFractions containing the desired compound together with a small amount of impurities
  6. concentrationconcentrated by distillation under reduced pressure
  7. customThe concentrate was again purified by column chromatography under the same conditions as above,

Sources & evidence

ORD record
ord-bb905b1f7ef042d9a55a9ed8627f64ce
Source dataset
uspto-grants-1997_03
Patent number
US05614550

Reaction notes

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