Hydrochloric Acid → HCID 69421516, compound

HRID 350289Notes

Reaction equation

HRID 350289 reaction equation
[C:1]1([C:7]2[C:11]([CH2:12][CH2:13][C:14]([O:16]CC)=[O:15])=[CH:10][N:9]([CH2:19][C:20]3[CH:21]=[CH:22][C:23]([O:26][CH2:27][C:28]4[N:29]=[C:30]([C:33]5[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=5)[S:31][CH:32]=4)=[N:24][CH:25]=3)[N:8]=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:11]([CH2:12][CH2:13][C:14]([OH:16])=[O:15])=[CH:10][N:9]([CH2:19][C:20]3[CH:25]=[N:24][C:23]([O:26][CH2:27][C:28]4[N:29]=[C:30]([C:33]5[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=5)[S:31][CH:32]=4)=[CH:22][CH:21]=3)[N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 69424500HCID 69424500, compound

Product 1

HCID 69421516HCID 69421516, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

After a mixture of ethyl 3-[3-phenyl-1-[2-(2-phenyl-4-thiazolylmethoxy)-5-pyridylmethyl]-1H-pyrazol-4-yl]propionate (603 mg), 1N sodium hydroxide solution (3 ml), tetrahydrofuran (6 ml), and ethanol (6 ml) was stirred at room temperature for 2 hours, 1N hydrochloric acid (3 ml) was added to the mixture, and 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-[3-phenyl-1-[6-(2-phenyl-4-thiazolylmethoxy)-3-pyridylmethyl]-1H-pyrazol-4-yl]propionic acid (500 mg, yield: 88%). This was recrystallized from acetone-hexane. Melting point: 107–108° 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-06c9249842214baeae378f83894975c4
Source dataset
uspto-grants-2007_02
Patent number
US07179823B1

Reaction notes

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