5-[5-(Benzyloxycarbonyl)furan-2-yl]-4-tert-butoxycarbonyl-4-pentenoic acid ethyl ester → 5-[2-(Tert-butoxycarbonyl)-5-ethoxy-5-oxopentyl]furan-2-carboxylic acid

HRID 332614Notes

Reaction equation

HRID 332614 reaction equation
[CH2:1]([O:3][C:4](=[O:31])[CH2:5][CH2:6][C:7]([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])=[CH:8][C:9]1[O:10][C:11]([C:14]([O:16]CC2C=CC=CC=2)=[O:15])=[CH:12][CH:13]=1)[CH3:2]>C(O)C.[Pd]>[C:27]([O:26][C:24]([CH:7]([CH2:6][CH2:5][C:4]([O:3][CH2:1][CH3:2])=[O:31])[CH2:8][C:9]1[O:10][C:11]([C:14]([OH:16])=[O:15])=[CH:12][CH:13]=1)=[O:25])([CH3:30])([CH3:29])[CH3:28]

Participants

4

Reactant 1

HCID 779345225-[5-(Benzyloxycarbonyl)furan-2-yl]-4-tert-butoxycarbonyl-4-pentenoic acid ethyl ester

Product 1

HCID 708692555-[2-(Tert-butoxycarbonyl)-5-ethoxy-5-oxopentyl]furan-2-carboxylic acid

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

5-[5-(Benzyloxycarbonyl)furan-2-yl]-4-tert-butoxycarbonyl-4-pentenoic acid ethyl ester obtained in step 2 was dissolved in ethanol (5 mL), a catalytic amount of 10% palladium/carbon was added, and the mixture was stirred at room temperature for 1 hour under a hydrogen atmosphere. The reaction mixture was filtered through celite, and the filtrate was concentrated under reduced pressure to give the title compound (82 mg).

Workup

  1. filtrationThe reaction mixture was filtered through celite
  2. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-1452dd3f00ec4377b23f5c81df1eff2f
Source dataset
uspto-grants-2014_11
Patent number
US08877805B2

Reaction notes

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