tert-Butyl 3-(3-(benzyloxy)-5-methylphenyl)-5-(2-tert-butoxy-2-oxoethyl)-4,5-dihydro-1,2-oxazole-5-carboxylate → tert-Butyl 5-(2-tert-butoxy-2-oxoethyl)-3-(3-hydroxy-5-methylphenyl)-4,5-dihydro-1,2-oxazole-5-carboxylate

HRID 1486882Notes

Reaction equation

HRID 1486882 reaction equation
C([O:8][C:9]1[CH:10]=[C:11]([C:16]2[CH2:20][C:19]([CH2:28][C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[O:18][N:17]=2)[CH:12]=[C:13]([CH3:15])[CH:14]=1)C1C=CC=CC=1.[H][H]>[Pd].C1COCC1>[C:32]([O:31][C:29](=[O:30])[CH2:28][C:19]1([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[O:18][N:17]=[C:16]([C:11]2[CH:12]=[C:13]([CH3:15])[CH:14]=[C:9]([OH:8])[CH:10]=2)[CH2:20]1)([CH3:34])([CH3:35])[CH3:33]

Participants

5

Reactant 2

HCID 118292885tert-Butyl 3-(3-(benzyloxy)-5-methylphenyl)-5-(2-tert-butoxy-2-oxoethyl)-4,5-dihydro-1,2-oxazole-5-carboxylateHCID 178418361HCID 178418361, compound

Product 1

HCID 118292757tert-Butyl 5-(2-tert-butoxy-2-oxoethyl)-3-(3-hydroxy-5-methylphenyl)-4,5-dihydro-1,2-oxazole-5-carboxylateYield 91.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of tert-butyl 3-(3-(benzyloxy)-5-methylphenyl)-5-(2-tert-butoxy-2-oxoethyl)-4,5-dihydro-1,2-oxazole-5-carboxylate (674 mg), 10% Pd/C (containing about 55% water, 67 mg), and THF (7 mL) was stirred overnight at room temperature in a hydrogen atmosphere. The catalyst was filtered off, and then, the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane) to obtain the title compound (500 mg).

Workup

  1. filtrationThe catalyst was filtered off
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customThe residue was purified by silica gel column chromatography (ethyl acetate/hexane)

Sources & evidence

ORD record
ord-37668759a2604abb897c21d178a39ecd
Source dataset
uspto-grants-2016_08
Patent number
US09428470B2

Reaction notes

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