HCID 53720994, compound → HCID 53729182, compound

HRID 1740496Notes

Reaction equation

HRID 1740496 reaction equation
[CH3:1][O:2][CH2:3][C@@H:4]1[O:8][C:7](=[O:9])[N:6]([C:10]2[C:14]3[CH:15]=[CH:16][C:17]([CH:19]=[CH:20][CH2:21][C@@H:22]([OH:27])[C:23]([F:26])([F:25])[F:24])=[CH:18][C:13]=3[O:12][CH:11]=2)[CH2:5]1>C(O)C.[Pd]>[CH3:1][O:2][CH2:3][C@@H:4]1[O:8][C:7](=[O:9])[N:6]([C:10]2[C:14]3[CH:15]=[CH:16][C:17]([CH2:19][CH2:20][CH2:21][C@@H:22]([OH:27])[C:23]([F:24])([F:25])[F:26])=[CH:18][C:13]=3[O:12][CH:11]=2)[CH2:5]1

Participants

4

Reactant 1

HCID 53720994HCID 53720994, compound

Product 1

HCID 53729182HCID 53729182, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

0.05 g of palladium-on-charcoal is added to a solution in 8.5 ml of ethanol of 0.26 g (0.67 mmol) of (R,R)-5-(methoxymethyl)-3-[6-(5,5,5-trifluoro-4-hydroxypent-1-enyl)benzofuran-3-yl]oxazolidin-2-one obtained in Example 8. The mixture is placed under a hydrogen atmosphere for 18 hours, the palladium-on-charcoal is removed by filtration and the filtrate is concentrated under reduced pressure. The product is then purifiedtran by chromatography on silica gel with a 60/40 mixture of cyclohexane and ethyl acetate. 0.14 g of product is recovered after crystallization from diisopropyl ether.

Workup

  1. customthe palladium-on-charcoal is removed by filtration
  2. concentrationthe filtrate is concentrated under reduced pressure
  3. additionThe product is then purifiedtran by chromatography on silica gel with a 60/40 mixture of cyclohexane and ethyl acetate
  4. custom0.14 g of product is recovered
  5. customafter crystallization from diisopropyl ether

Sources & evidence

ORD record
ord-09d7b9fd980c4aaca8bf341176854aae
Source dataset
uspto-grants-1999_10
Patent number
US05969146

Reaction notes

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