Hydrochloric Acid → HCID 69424004, compound

HRID 350272Notes

Reaction equation

HRID 350272 reaction equation
[C:1]1([C:7]2[CH:8]=[CH:9][C:10]([CH2:13][O:14][C:15]3[CH:39]=[CH:38][C:18]([CH2:19][N:20]4[CH:24]=[C:23]([C:25]5[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=5)[C:22]([CH2:31][CH2:32][C:33]([O:35]CC)=[O:34])=[CH:21]4)=[CH:17][CH:16]=3)=[N:11][CH:12]=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[CH:8]=[CH:9][C:10]([CH2:13][O:14][C:15]3[CH:39]=[CH:38][C:18]([CH2:19][N:20]4[CH:24]=[C:23]([C:25]5[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=5)[C:22]([CH2:31][CH2:32][C:33]([OH:35])=[O:34])=[CH:21]4)=[CH:17][CH:16]=3)=[N:11][CH:12]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 69424051HCID 69424051, compound

Product 1

HCID 69424004HCID 69424004, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

After a mixture of ethyl 3-[1-[4-(5-phenyl-2-pyridylmethoxy)benzyl]-4-phenyl-3-pyrrolyl]propionate (1020 mg), 1N aqueous sodium hydroxide solution (4 ml), tetrahydrofuran (5 ml) and ethanol (5 ml) was stirred at room temperature for 2 hours, 1 N hydrochloric acid (4 ml) was added to the mixture, and then the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with saturated aqueous sodium chloride solution, dried (MgSO4) and concentrated. The resulting colorless crystals were collected by filtration to obtain 3-[1-[4-(5-phenyl-2-pyridylmethoxy)benzyl]-4-phenyl-3-pyrrolyl]propionic acid (930 mg, yield: 97%). This was recrystallized from acetone-hexane. Melting point: 169–170° C.

Workup

  1. extractionthe mixture was 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. filtrationThe resulting colorless crystals were collected by filtration

Sources & evidence

ORD record
ord-8a25db71abad4d8084d73711f78df935
Source dataset
uspto-grants-2007_02
Patent number
US07179823B1

Reaction notes

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