Hydrochloric Acid → HCID 69421759, compound

HRID 350242Notes

Reaction equation

HRID 350242 reaction equation
[Cl:1][C:2]1[C:3]([CH2:14][O:15][C:16]2[CH:37]=[CH:36][C:19]([CH2:20][N:21]3[CH:25]=[C:24]([CH2:26][CH2:27][C:28]([O:30]CC)=[O:29])[C:23]([O:33][CH2:34][CH3:35])=[N:22]3)=[CH:18][CH:17]=2)=[N:4][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[CH:6][CH:7]=1.[OH-].[Na+].O1CCCC1.Cl>C(O)C>[Cl:1][C:2]1[C:3]([CH2:14][O:15][C:16]2[CH:37]=[CH:36][C:19]([CH2:20][N:21]3[CH:25]=[C:24]([CH2:26][CH2:27][C:28]([OH:30])=[O:29])[C:23]([O:33][CH2:34][CH3:35])=[N:22]3)=[CH:18][CH:17]=2)=[N:4][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 69420165HCID 69420165, compound

Product 1

HCID 69421759HCID 69421759, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

After a mixture of ethyl 3-[1-[4-(3-chloro-6-phenyl-2-pyridylmethoxy)benzyl]-3-ethoxy-1H-pyrazol-4-yl]propionate (738 mg), 1N aqueous sodium hydroxide solution (3 ml), tetrahydrofuran (6 ml) and ethanol (6 ml) was stirred at room temperature for 3 hours, 1 N hydrochloric acid (3 ml) was added to the mixture, and then the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with a saturated aqueous sodium chloride solution, dried (MgSO4) and concentrated. The resulting colorless crystals were collected by filtration to obtain 3-[1-[4-(3-chloro-6-phenyl-2-pyridylmethoxy)benzyl]-3-ethoxy-1H-pyrazol-4-yl]propionic acid (669 mg, yield: 96%). This was recrystallized from ethyl acetate-hexane. Melting point: 120–121° C.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe ethyl acetate layer was washed with a 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-523d89ae1c6e4171a40f4a419d0b8e4a
Source dataset
uspto-grants-2007_02
Patent number
US07179823B1

Reaction notes

Loading…