tert-Butyl 3-(3-(benzyloxy)-5-((1E)-3-tert-butoxy-3-oxoprop-1-en-1-yl)phenyl)-5-(2-tert-butoxy-2-oxoethyl)-4,5-dihydro-1,2-oxazole-5-carboxylate → tert-Butyl 5-(2-tert-butoxy-2-oxoethyl)-3-(3-(3-tert-butoxy-3-oxopropyl)-5-hydroxyphenyl)-4,5-dihydro-1,2-oxazole-5-carboxylate

HRID 1486888Notes

Reaction equation

HRID 1486888 reaction equation
C([O:8][C:9]1[CH:10]=[C:11]([C:24]2[CH2:28][C:27]([CH2:36][C:37]([O:39][C:40]([CH3:43])([CH3:42])[CH3:41])=[O:38])([C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])[O:26][N:25]=2)[CH:12]=[C:13](/[CH:15]=[CH:16]/[C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH:14]=1)C1C=CC=CC=1>[Pd].C1COCC1>[C:40]([O:39][C:37](=[O:38])[CH2:36][C:27]1([C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])[O:26][N:25]=[C:24]([C:11]2[CH:10]=[C:9]([OH:8])[CH:14]=[C:13]([CH2:15][CH2:16][C:17]([O:19][C:20]([CH3:21])([CH3:23])[CH3:22])=[O:18])[CH:12]=2)[CH2:28]1)([CH3:41])([CH3:42])[CH3:43]

Participants

4

Reactant 1

HCID 118292792tert-Butyl 3-(3-(benzyloxy)-5-((1E)-3-tert-butoxy-3-oxoprop-1-en-1-yl)phenyl)-5-(2-tert-butoxy-2-oxoethyl)-4,5-dihydro-1,2-oxazole-5-carboxylate

Product 1

HCID 118292873tert-Butyl 5-(2-tert-butoxy-2-oxoethyl)-3-(3-(3-tert-butoxy-3-oxopropyl)-5-hydroxyphenyl)-4,5-dihydro-1,2-oxazole-5-carboxylateYield 72.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of tert-butyl 3-(3-(benzyloxy)-5-((1E)-3-tert-butoxy-3-oxoprop-1-en-1-yl)phenyl)-5-(2-tert-butoxy-2-oxoethyl)-4,5-dihydro-1,2-oxazole-5-carboxylate (272 mg), 10% Pd/C (containing about 55% water, 27 mg), and THF (3 mL) was stirred at room temperature for 3 hours under a hydrogen atmosphere. The catalyst was filtered off, and then, the filtrate was concentrated under reduced pressure. The residue was combined with 10% Pd/C (containing about 55% water, 54 mg) and THF (3 mL), and the obtained mixture was stirred at room temperature for 2 hours under a hydrogen atmosphere. The catalyst was filtered off, and then, the filtrate was concentrated under reduced pressure. The residue was combined with 10% Pd/C (containing about 55% water, 81 mg) and THF (3 mL), and the obtained mixture was stirred overnight at room temperature under 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 (167 mg).

Workup

  1. filtrationThe catalyst was filtered off
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. stirringthe obtained mixture was stirred at room temperature for 2 hours under a hydrogen atmosphere
  4. filtrationThe catalyst was filtered off
  5. concentrationthe filtrate was concentrated under reduced pressure
  6. stirringthe obtained mixture was stirred overnight at room temperature under a hydrogen atmosphere
  7. filtrationThe catalyst was filtered off
  8. concentrationthe filtrate was concentrated under reduced pressure
  9. customThe residue was purified by silica gel column chromatography (ethyl acetate/hexane)

Sources & evidence

ORD record
ord-a552b79cc0eb4a4798ebf52ab00eaece
Source dataset
uspto-grants-2016_08
Patent number
US09428470B2

Reaction notes

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