Benzyl (2E)-3-(4-(benzyloxy)-2-(5,5-bis(2-methoxy-2-oxoethyl)-4,5-dihydro-1,2-oxazol-3-yl)phenyl)acrylate → 3-(2-(5,5-Bis(2-methoxy-2-oxoethyl)-4,5-dihydro-1,2-oxazol-3-yl)-4-hydroxyphenyl)propanoic acid

HRID 1486904Notes

Reaction equation

HRID 1486904 reaction equation
C([O:8][C:9]1[CH:14]=[CH:13][C:12](/[CH:15]=[CH:16]/[C:17]([O:19]CC2C=CC=CC=2)=[O:18])=[C:11]([C:27]2[CH2:31][C:30]([CH2:37][C:38]([O:40][CH3:41])=[O:39])([CH2:32][C:33](=[O:36])[O:34][CH3:35])[O:29][N:28]=2)[CH:10]=1)C1C=CC=CC=1>[Pd].C1COCC1>[CH3:41][O:40][C:38](=[O:39])[CH2:37][C:30]1([CH2:32][C:33](=[O:36])[O:34][CH3:35])[O:29][N:28]=[C:27]([C:11]2[CH:10]=[C:9]([OH:8])[CH:14]=[CH:13][C:12]=2[CH2:15][CH2:16][C:17]([OH:19])=[O:18])[CH2:31]1

Participants

4

Reactant 1

HCID 131736835Benzyl (2E)-3-(4-(benzyloxy)-2-(5,5-bis(2-methoxy-2-oxoethyl)-4,5-dihydro-1,2-oxazol-3-yl)phenyl)acrylate

Product 1

HCID 1182927643-(2-(5,5-Bis(2-methoxy-2-oxoethyl)-4,5-dihydro-1,2-oxazol-3-yl)-4-hydroxyphenyl)propanoic acidYield 100%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of benzyl (2E)-3-(4-(benzyloxy)-2-(5,5-bis(2-methoxy-2-oxoethyl)-4,5-dihydro-1,2-oxazol-3-yl)phenyl)acrylate (2.47 g), 10% Pd/C (containing about 55% water, 250 mg), and THF (25 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 to obtain the title compound (1.680 g).

Workup

  1. filtrationThe catalyst was filtered off
  2. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-af8b3b763e164d14a1fddafb02508c2c
Source dataset
uspto-grants-2016_08
Patent number
US09428470B2

Reaction notes

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