Hydrochloric Acid → HCID 178426485, compound

HRID 1893368Notes

Reaction equation

HRID 1893368 reaction equation
C([O:3][C:4]([C@H:6]1[CH2:11][CH2:10][C@H:9]([N:12]2[C:16]([CH3:17])=[CH:15][C:14]([CH3:18])=[N:13]2)[CH2:8][CH2:7]1)=[O:5])C.[OH-].[Na+].Cl>O1CCOCC1>[CH3:18][C:14]1[CH:15]=[C:16]([CH3:17])[N:12]([C@H:9]2[CH2:10][CH2:11][C@H:6]([C:4]([OH:5])=[O:3])[CH2:7][CH2:8]2)[N:13]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 178472399HCID 178472399, compound

Product 1

HCID 178426485HCID 178426485, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A solution of trans-4-(3,5-dimethyl-pyrazol-1-yl)-cyclohexanecarboxylic acid ethyl ester (162 mg, 0.647 mmol) in 1,4-dioxane (6.5 ml) and 2 M aqueous sodium hydroxide solution (3.2 ml, 6.4 mmol) was stirred at room temperature for 15 h. The pH was adjusted to 3 by addition of 2 M aqueous hydrochloric acid. The mixture was partitioned between ethyl acetate (25 ml) and water (25 ml). The layers were separated. The aqueous layer was extracted with two 25-ml portions of ethyl acetate. The combined organic layers were dried over anhydrous sodium sulfate and concentrated in vacuo to give the title compound (116 mg, 81%) as light brown solid. MS m/e: 221 ([M−H]−)

Workup

  1. customThe mixture was partitioned between ethyl acetate (25 ml) and water (25 ml)
  2. customThe layers were separated
  3. extractionThe aqueous layer was extracted with two 25-ml portions of ethyl acetate
  4. dry with materialThe combined organic layers were dried over anhydrous sodium sulfate
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-f9196e84fbf44f099d038d8d5f014b25
Source dataset
uspto-grants-2013_08
Patent number
US08513238B2

Reaction notes

Loading…