HCID 54504049, compound → HCID 18997213, compound

HRID 374510Notes

Reaction equation

HRID 374510 reaction equation
[C:1]1([N:7]2[CH2:11][CH:10]([CH2:12][O:13][C:14]3[CH:25]=[CH:24][C:17]([CH:18]=[CH:19][C:20]([O:22][CH3:23])=[O:21])=[CH:16][CH:15]=3)[O:9][C:8]2=[O:26])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H][H]>[C].[Pd].O1CCCC1>[C:1]1([N:7]2[CH2:11][CH:10]([CH2:12][O:13][C:14]3[CH:25]=[CH:24][C:17]([CH2:18][CH2:19][C:20]([O:22][CH3:23])=[O:21])=[CH:16][CH:15]=3)[O:9][C:8]2=[O:26])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 2

HCID 54504049HCID 54504049, compound2×HCID 178418361HCID 178418361, compound

Product 1

HCID 18997213HCID 18997213, compoundYield 90.3%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A 200 mg quantity of 10% palladium carbon was added to a tetrahydrofuran (50 ml) solution of 1.75 g of methyl 4-(3-phenyl-2-oxooxazolidin-5-yl)methoxycinnamate (compound 185) obtained in Example 29. The mixture was stirred at room temperature for 2.5 hours in a stream of hydrogen at 3 atmospheric pressure. The reaction mixture was filtered, and the filtrate was concentrated under reduced pressure and washed with methanol to give 1.59 g of the title compound (compound 189) in a yield of 88%.

Workup

  1. customobtained in Example 29
  2. filtrationThe reaction mixture was filtered
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. washwashed with methanol

Sources & evidence

ORD record
ord-86aa0818fbf7488890bbc6360b12db7b
Source dataset
uspto-grants-1996_01
Patent number
US05480899

Reaction notes

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