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

HRID 1486892Notes

Reaction equation

HRID 1486892 reaction equation
C([O:8][C:9]1[CH:10]=[CH:11][C:12](/[CH:35]=[CH:36]/[C:37]([O:39]CC2C=CC=CC=2)=[O:38])=[C:13]([C:15]2[CH2:19][C:18]([CH2:27][C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[O:17][N:16]=2)[CH:14]=1)C1C=CC=CC=1>[Pd].C1COCC1>[C:23]([O:22][C:20]([C:18]1([CH2:27][C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])[O:17][N:16]=[C:15]([C:13]2[CH:14]=[C:9]([OH:8])[CH:10]=[CH:11][C:12]=2[CH2:35][CH2:36][C:37]([OH:39])=[O:38])[CH2:19]1)=[O:21])([CH3:25])([CH3:26])[CH3:24]

Participants

4

Reactant 1

HCID 118292836tert-Butyl 3-(5-(benzyloxy)-2-((1E)-3-(benzyloxy)-3-oxoprop-1-en-1-yl)phenyl)-5-(2-tert-butoxy-2-oxoethyl)-4,5-dihydro-1,2-oxazole-5-carboxylate

Product 1

HCID 1182928123-(2-(5-(tert-Butoxycarbonyl)-5-(2-tert-butoxy-2-oxoethyl)-4,5-dihydro-1,2-oxazol-3-yl)-4-hydroxyphenyl)propanoic acidYield 114.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of tert-butyl 3-(5-(benzyloxy)-2-((1E)-3-(benzyloxy)-3-oxoprop-1-en-1-yl)phenyl)-5-(2-tert-butoxy-2-oxoethyl)-4,5-dihydro-1,2-oxazole-5-carboxylate (260 mg), 10% Pd/C (containing about 55% water, 26 mg), and THF (3 mL) 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 combined with 10% Pd/C (containing about 55% water, 52 mg) and THF (3 mL), and the obtained mixture 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 to obtain the title compound (214 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 3 hours under a hydrogen atmosphere
  4. filtrationThe catalyst was filtered off
  5. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-add145f999aa4f798bc1cd4eae137254
Source dataset
uspto-grants-2016_08
Patent number
US09428470B2

Reaction notes

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