HCID 20775651, compound → HCID 86759661, compound

HRID 1815997Notes

Reaction equation

HRID 1815997 reaction equation
C([O:8][C:9]([C:11]1[N:12]=[C:13]([CH:16]([CH2:22][C:23]2[CH:28]=[CH:27][C:26]([O:29][C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])=[CH:25][CH:24]=2)[CH2:17][C:18]([O:20][CH3:21])=[O:19])[O:14][CH:15]=1)=[O:10])C1C=CC=CC=1>CCO.[Pd]>[C:9]([C:11]1[N:12]=[C:13]([CH:16]([CH2:22][C:23]2[CH:24]=[CH:25][C:26]([O:29][C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])=[CH:27][CH:28]=2)[CH2:17][C:18]([O:20][CH3:21])=[O:19])[O:14][CH:15]=1)([OH:10])=[O:8]

Participants

4

Reactant 1

HCID 20775651HCID 20775651, compound

Product 1

HCID 86759661HCID 86759661, compoundYield 105.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of methyl (±)-3-[4-(benzyloxycarbonyl)-1,3-oxazol-2-yl]-4-[4-[(tert-butyloxycarbonyl)oxy]phenyl]butanoate (765 mg, 1.54 mmole) and 10% Pd/C (164 mg) in EtOH (20 mL) was deoxygenated (3×evacuation/N2 purge cycles) then was charged with H2 (50 psi). After 4 hr the H2 was removed and the mixture was filtered through a pad of celite®. The filtrate was concentrated to afford the title compound (659 mg, 100%) as a white solid: MS (ES) m/e 811 (2M+H)+.

Workup

  1. customwas deoxygenated
  2. custom(3×evacuation/N2 purge cycles)
  3. additionthen was charged with H2 (50 psi)
  4. customAfter 4 hr the H2 was removed
  5. filtrationthe mixture was filtered through a pad of celite®
  6. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-d894f1d6ee4640c3bf75c8a569e0bce5
Source dataset
uspto-grants-2005_04
Patent number
US06881736B1

Reaction notes

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