Hydrochloric Acid → HCID 69427141, compound

HRID 350293Notes

Reaction equation

HRID 350293 reaction equation
[CH3:1][C:2]1[O:6][C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[N:4][C:3]=1[CH2:13][O:14][C:15]1[CH:16]=[CH:17][C:18]([CH2:21][N:22]2[CH:26]=[C:25]([CH2:27][CH2:28][C:29]([O:31]CC)=[O:30])[C:24]([C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=3)=[N:23]2)=[N:19][CH:20]=1.[OH-].[Na+].O1CCCC1.Cl>C(O)C>[CH3:1][C:2]1[O:6][C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[N:4][C:3]=1[CH2:13][O:14][C:15]1[CH:16]=[CH:17][C:18]([CH2:21][N:22]2[CH:26]=[C:25]([CH2:27][CH2:28][C:29]([OH:31])=[O:30])[C:24]([C:34]3[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=3)=[N:23]2)=[N:19][CH:20]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 69423092HCID 69423092, compound

Product 1

HCID 69427141HCID 69427141, compoundYield 94.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

After a mixture of ethyl 3-[1-[5-(5-methyl-2-phenyl-4-oxazolylmethoxy)-2-pyridylmethyl]-3-phenyl-1H-pyrazol-4-yl]propionate (930 mg), 1N sodium hydroxide solution (3 ml), tetrahydrofuran (5 ml), and ethanol (5 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-[1-[5-(5-methyl-2-phenyl-4-oxazolylmethoxy)-2-pyridylmethyl]-3-phenyl-1H-pyrazol-4-yl]propionic acid (830 mg, yield: 94%). This was recrystallized from acetone-hexane. Melting point: 175–176° 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-9ad370eb491a4518b26f89511c082410
Source dataset
uspto-grants-2007_02
Patent number
US07179823B1

Reaction notes

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