Hydrochloric Acid → 3-[1-[6-(2-Fluorobenzyloxy)-2-naphthylmethyl]-4-phenyl-3-pyrrolyl]propionic acid

HRID 350081

Reaction equation

HRID 350081 reaction equation
[F:1][C:2]1[CH:38]=[CH:37][CH:36]=[CH:35][C:3]=1[CH2:4][O:5][C:6]1[CH:7]=[C:8]2[C:13](=[CH:14][CH:15]=1)[CH:12]=[C:11]([CH2:16][N:17]1[CH:21]=[C:20]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[C:19]([CH2:28][CH2:29][C:30]([O:32]CC)=[O:31])=[CH:18]1)[CH:10]=[CH:9]2.[OH-].[Na+].O1CCCC1.Cl>C(O)C>[F:1][C:2]1[CH:38]=[CH:37][CH:36]=[CH:35][C:3]=1[CH2:4][O:5][C:6]1[CH:7]=[C:8]2[C:13](=[CH:14][CH:15]=1)[CH:12]=[C:11]([CH2:16][N:17]1[CH:21]=[C:20]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[C:19]([CH2:28][CH2:29][C:30]([OH:32])=[O:31])=[CH:18]1)[CH:10]=[CH:9]2

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 69422683Ethyl 3-[1-[6-(2-fluorobenzyloxy)-2-naphthylmethyl]-4-phenyl-3-pyrrolyl]propionate

Product 1

HCID 694217493-[1-[6-(2-Fluorobenzyloxy)-2-naphthylmethyl]-4-phenyl-3-pyrrolyl]propionic acidYield 76.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of ethyl 3-[1-[6-(2-fluorobenzyloxy)-2-naphthylmethyl]-4-phenyl-3-pyrrolyl]propionate (401 mg), 1N aqueous sodium hydroxide solution (2 ml), tetrahydrofuran (4 ml) and ethanol (4 ml) was stirred at room temperature for 7 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-[6-(2-fluorobenzyloxy)-2-naphthylmethyl]-4-phenyl-3-pyrrolyl]propionic acid (289 mg, yield: 76%). This was recrystallized from ethanol-hexane. Melting point: 143–144° 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-433cdff2a37245fdb1bae7d4b18cb610
Source dataset
uspto-grants-2007_02
Patent number
US07179823B1

Linked notes

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