HCID 54068121, compound → HCID 70107262, compound

HRID 977238Notes

Reaction equation

HRID 977238 reaction equation
[CH3:1][C:2]1[O:6][C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[N:4][C:3]=1[CH2:13][CH2:14][C:15]([C:17]1[CH:30]=[CH:29][C:20]([CH:21]=[C:22]2[O:26][C:25](=[O:27])[NH:24][C:23]2=[O:28])=[CH:19][CH:18]=1)=[O:16]>[C].[Pd].O1CCCC1>[OH:16][CH:15]([C:17]1[CH:30]=[CH:29][C:20]([CH2:21][CH:22]2[O:26][C:25](=[O:27])[NH:24][C:23]2=[O:28])=[CH:19][CH:18]=1)[CH2:14][CH2:13][C:3]1[N:4]=[C:5]([C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=2)[O:6][C:2]=1[CH3:1]

Participants

4

Reactant 1

HCID 54068121HCID 54068121, compound

Product 1

HCID 70107262HCID 70107262, compoundYield 53%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 5-[4-[3-(5-methyl-2-phenyl-4-oxazolyl)propionyl]benzylidene]-2,4-oxazolidinedione (0.75 g), palladium-carbon (5%, 0.75 g) and tetrahydrofuran (THF) (70 ml) was subjected to catalytic hydrogenation at 3 atm and room temperature. After the catalyst was filtered out, the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography. From the fraction eluted with chloroform-ethyl acetate (1:1, v/v), 5-[4-[1-hydroxy-3-(5-methyl-2-phenyl-4-oxazolyl)propyl]benzyl]-2,4-oxazolidinedione (0.4 g, 53%) was obtained, which was then recrystallized from dichloromethane-methanol-isopropyl ether to yield colorless needles having a melting point of 154°-155° C.

Workup

  1. customwas subjected to catalytic hydrogenation at 3 atm and room temperature
  2. filtrationAfter the catalyst was filtered out
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. customThe residue was purified by silica gel column chromatography
  5. washFrom the fraction eluted with chloroform-ethyl acetate (1:1

Sources & evidence

ORD record
ord-0753f70457bf4b0a920b76de52f0a4f6
Source dataset
uspto-grants-1997_03
Patent number
US05614544

Reaction notes

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