Hydrochloric Acid → 3-[1-[4-(2-Methyl-4-thiazolylmethoxy]benzyl]-4-phenyl-3-pyrrolyl]propionic acid

HRID 350068Notes

Reaction equation

HRID 350068 reaction equation
[CH3:1][C:2]1[S:3][CH:4]=[C:5]([CH2:7][O:8][C:9]2[CH:33]=[CH:32][C:12]([CH2:13][N:14]3[CH:18]=[C:17]([C:19]4[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=4)[C:16]([CH2:25][CH2:26][C:27]([O:29]CC)=[O:28])=[CH:15]3)=[CH:11][CH:10]=2)[N:6]=1.[OH-].[Na+].O1CCCC1.Cl>C(O)C>[CH3:1][C:2]1[S:3][CH:4]=[C:5]([CH2:7][O:8][C:9]2[CH:10]=[CH:11][C:12]([CH2:13][N:14]3[CH:18]=[C:17]([C:19]4[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=4)[C:16]([CH2:25][CH2:26][C:27]([OH:29])=[O:28])=[CH:15]3)=[CH:32][CH:33]=2)[N:6]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 69420192Ethyl 3-[1-[4-(2-methyl-4-thiazolylmethoxy)benzyl]-4-phenyl-3-pyrrolyl]propionate

Product 1

HCID 694216903-[1-[4-(2-Methyl-4-thiazolylmethoxy]benzyl]-4-phenyl-3-pyrrolyl]propionic acidYield 73%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of ethyl 3-[1-[4-(2-methyl-4-thiazolylmethoxy]benzyl]-4-phenyl-3-pyrrolyl]propionate (368 mg), 1N aqueous sodium hydroxide solution (2 ml), tetrahydrofuran (4 ml), and ethanol (4 ml) was stirred at room temperature for 4 hours, and 1N hydrochloric acid (2 ml) was added to the mixture, which was extracted with ethyl acetate. The ethyl acetate layer was washed with saturated aqueous sodium chloride solution, dried (MgSO4), then concentrated. The colorless crystals obtained were collected by filtration to yield 3-[1-[4-(2-methyl-4-thiazolylmethoxy]benzyl]-4-phenyl-3-pyrrolyl]propionic acid (251 mg, yield: 73%). This was recrystallized from ethanol-hexane. Melting point: 113–114° 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. customThe colorless crystals obtained
  6. filtrationwere collected by filtration

Sources & evidence

ORD record
ord-5eab91ef9e774564a59db4bb00de2dfd
Source dataset
uspto-grants-2007_02
Patent number
US07179823B1

Reaction notes

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