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 517345Notes

Reaction equation

HRID 517345 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-ad9e52d013f9432094d3a6de08a443c2
Source dataset
uspto-grants-2015_08
Patent number
US09115107B2

Reaction notes

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