Hydrochloric Acid → 3-[1-(4-Benzyloxybenzyl)-4-phenyl-3-pyrrolyl]propionic acid

HRID 350038Notes

Reaction equation

HRID 350038 reaction equation
[OH:1][C:2]1[CH:26]=[CH:25][C:5]([CH2:6][N:7]2[CH:11]=[C:10]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[C:9]([CH2:18][CH2:19][C:20]([O:22]CC)=[O:21])=[CH:8]2)=[CH:4][CH:3]=1.[CH2:27](Br)[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1.C(=O)([O-])[O-].[K+].[K+].Cl.[OH-].[Na+]>C(O)C.O1CCCC1.CN(C)C=O>[CH2:27]([O:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][N:7]2[CH:11]=[C:10]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[C:9]([CH2:18][CH2:19][C:20]([OH:22])=[O:21])=[CH:8]2)=[CH:25][CH:26]=1)[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1

Participants

9

Reactant 5

HCID 313Hydrochloric AcidHCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 14798Sodium HydroxideHCID 23024736Ethyl 3-[1-(4-hydroxybenzyl)-4-phenyl-3-pyrrolyl]propionate

Product 1

HCID 694229233-[1-(4-Benzyloxybenzyl)-4-phenyl-3-pyrrolyl]propionic acidYield 84%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of ethyl 3-[1-(4-hydroxybenzyl)-4-phenyl-3-pyrrolyl]propionate (1.55 g), benzyl bromide (0.7 ml), potassium carbonate (0.92 g) and N,N-dimethylformamide (15 ml) was stirred at room temperature overnight. The reaction mixture was poured into dilute hydrochloric acid, which was extracted with ethyl acetate. The ethyl acetate layer was washed with saturated aqueous sodium chloride solution, dried (MgSO4), and then concentrated. The residue was subjected to silica gel column chromatography, and an oily substance was obtained from the fraction eluted with ethyl acetate-hexane (1:4, volume ratio). A mixture of the oily substance obtained, 1N aqueous sodium hydroxide solution (8 ml), tetrahydrofuran (8 ml) and ethanol (8 ml) was stirred at room temperature for 3 hours and the organic solvent was removed under reduced pressure. After adding water, the residue was acidified by adding 1N hydrochloric acid. The colorless crystals obtained were collected by filtration to yield 3-[1-(4-benzyloxybenzyl)-4-phenyl-3-pyrrolyl]propionic acid (1.53 g, yield: 84%). This was recrystallized from ethyl acetate-hexane. Melting point: 130–131° C.

Workup

  1. extractionwas extracted with ethyl acetate
  2. washThe ethyl acetate layer was washed with saturated aqueous sodium chloride solution
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated
  5. customan oily substance was obtained from the fraction
  6. washeluted with ethyl acetate-hexane (1:4, volume ratio)
  7. additionA mixture of the oily substance
  8. customobtained
  9. customthe organic solvent was removed under reduced pressure
  10. additionAfter adding water
  11. additionby adding 1N hydrochloric acid
  12. customThe colorless crystals obtained
  13. filtrationwere collected by filtration

Sources & evidence

ORD record
ord-b134e5b71f8a4c9c90826d115e531654
Source dataset
uspto-grants-2007_02
Patent number
US07179823B1

Reaction notes

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