Hydrochloric Acid → HCID 10278715, compound

HRID 350324Notes

Reaction equation

HRID 350324 reaction equation
[C:1]1([C:7]2[S:8][CH:9]=[C:10]([CH2:12][O:13][C:14]3[CH:42]=[CH:41][C:17]([CH2:18][N:19]4[CH:23]=[C:22]([CH2:24][CH:25](C(OCC)=O)[C:26]([O:28]CC)=[O:27])[C:21]([C:36]5[S:37][CH:38]=[CH:39][CH:40]=5)=[N:20]4)=[CH:16][CH:15]=3)[N: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[S:8][CH:9]=[C:10]([CH2:12][O:13][C:14]3[CH:42]=[CH:41][C:17]([CH2:18][N:19]4[CH:23]=[C:22]([CH2:24][CH2:25][C:26]([OH:28])=[O:27])[C:21]([C:36]5[S:37][CH:38]=[CH:39][CH:40]=5)=[N:20]4)=[CH:16][CH:15]=3)[N:11]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 70123192HCID 70123192, compound

Product 1

HCID 10278715HCID 10278715, compoundYield 95.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
110 °C

Procedure

A mixture of diethyl [1-[4-(2-phenyl-4-thiazolylmethoxy)benzyl]-3-(2-thienyl)-1H-pyrazol-4-yl]methylmalonate (4.09 g), 1N aqueous sodium hydroxide solution (30 ml), tetrahydrofuran (30 ml), and ethanol (30 ml) was refluxed for 1 hour. After cooling, 1N hydrochloric acid (30 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 oily substance was dissolved in pyridine (50 ml), and the mixture was stirred at 110° C. for 2 hours. After removing pyridine under reduced pressure, ethyl acetate was added to the residue. The resulting solution was washed successively with dilute hydrochloric acid and saturated aqueous sodium chloride solution, dried (MgSO4), and concentrated. The resulting colorless crystals were collected by filtration to obtain 3-[1-[4-(2-phenyl-4-thiazolylmethoxy)benzyl]-3-(2-thienyl)-1H-pyrazol-4-yl]propionic acid (3.25 g, yield: 95%). This was recrystallized from ethyl acetate-hexane. Melting point: 133˜134° C.

Workup

  1. temperaturewas refluxed for 1 hour
  2. temperatureAfter cooling
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe ethyl acetate layer was washed with saturated aqueous sodium chloride solution
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated
  7. dissolutionThe resulting colorless oily substance was dissolved in pyridine (50 ml)
  8. customAfter removing pyridine under reduced pressure, ethyl acetate
  9. additionwas added to the residue
  10. washThe resulting solution was washed successively with dilute hydrochloric acid and saturated aqueous sodium chloride solution
  11. dry with materialdried (MgSO4)
  12. concentrationconcentrated
  13. filtrationThe resulting colorless crystals were collected by filtration

Sources & evidence

ORD record
ord-0f4543e08eb845a08df095653d77a0a0
Source dataset
uspto-grants-2007_02
Patent number
US07179823B1

Reaction notes

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