HCID 57195348, compound → HCID 10961013, compound

HRID 977231Notes

Reaction equation

HRID 977231 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:32]=[CH:31][C:20]([CH:21]=[CH:22][CH:23]=[C:24]2[O:28][C:27](=[O:29])[NH:26][C:25]2=[O:30])=[CH:19][CH:18]=1)=[O:16]>[C].[Pd].O1CCCC1>[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:32]=[CH:31][C:20]([CH2:21][CH2:22][CH2:23][CH:24]2[O:28][C:27](=[O:29])[NH:26][C:25]2=[O:30])=[CH:19][CH:18]=1)=[O:16]

Participants

4

Reactant 1

HCID 57195348HCID 57195348, compound

Product 1

HCID 10961013HCID 10961013, compoundYield 56.3%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 5-[4-[3-(5-methyl-2-phenyl-4-oxazolyl)propionyl]cinnamylidene]-2,4-oxazolidinedione (1.02 g), palladium-carbon (5%, 0.5 g) and tetrahydrofuran (THF) (150 ml) was subjected to catalytic hydrogenation at 1 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-methanol (100:3), 5-[3-[4-[3-(5-methyl-2-phenyl-4-oxazolyl)propionyl]phenyl]propyl]-2,4-oxazolidinedione (0.58 g, 56%) was obtained, which was then recrystallized from dichloromethane-methanol to yield colorless needles having a melting point of 184°-185° C.

Workup

  1. customwas subjected to catalytic hydrogenation at 1 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-methanol (100:3)

Sources & evidence

ORD record
ord-fa314f00b14d43f89628b14bb7e7b3b0
Source dataset
uspto-grants-1997_03
Patent number
US05614544

Reaction notes

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