Hydrochloric Acid → HCID 69422697, compound

HRID 350048Notes

Reaction equation

HRID 350048 reaction equation
[C:1]1([C:7]2[C:8]([CH2:26][CH2:27][C:28]([O:30]CC)=[O:29])=[CH:9][N:10]([CH2:12][C:13]3[CH:18]=[CH:17][C:16]([O:19][CH2:20][C:21]4[CH:25]=[CH:24][S:23][CH:22]=4)=[CH:15][CH:14]=3)[CH:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH-].[Na+].O1CCCC1.Cl>C(O)C>[C:1]1([C:7]2[C:8]([CH2:26][CH2:27][C:28]([OH:30])=[O:29])=[CH:9][N:10]([CH2:12][C:13]3[CH:18]=[CH:17][C:16]([O:19][CH2:20][C:21]4[CH:25]=[CH:24][S:23][CH:22]=4)=[CH:15][CH:14]=3)[CH:11]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 23024820HCID 23024820, compound

Product 1

HCID 69422697HCID 69422697, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of ethyl 3-[4-phenyl-1-[4-(3-thienylmethoxy)benzyl]-3-pyrrolyl]propionate (624 mg), 1N aqueous sodium hydroxide solution (3 ml), tetrahydrofuran (6 ml), and ethanol (6 ml) was stirred at room temperature for 5 hours, and 1N hydrochloric acid (3 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), and then concentrated. The colorless crystals obtained were collected by filtration to yield 3-[4-phenyl-1-[4-(3-thienylmethoxy)benzyl]-3-pyrrolyl]propionic acid (421 mg, yield: 72%). This was recrystallized from ethyl acetate-hexane. Melting point: 118–119° 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-5917f271aacc4507acf7db79885db4f1
Source dataset
uspto-grants-2007_02
Patent number
US07179823B1

Reaction notes

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