Hydrochloric Acid → HCID 178525743, compound

HRID 1893367Notes

Reaction equation

HRID 1893367 reaction equation
C([O:3][C:4]([C@H:6]1[CH2:11][CH2:10][C@@H:9]([N:12]2[CH:16]=[CH:15][CH:14]=[N:13]2)[CH2:8][CH2:7]1)=[O:5])C.[OH-].[Na+].Cl>O1CCOCC1>[N:12]1([C@@H:9]2[CH2:8][CH2:7][C@H:6]([C:4]([OH:5])=[O:3])[CH2:11][CH2:10]2)[CH:16]=[CH:15][CH:14]=[N:13]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 178472383HCID 178472383, compound

Product 1

HCID 178525743HCID 178525743, compoundYield 95.3%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A solution of cis-4-pyrazol-1-yl-cyclohexanecarboxylic acid ethyl ester (95 mg, 0.427 mmol) in 1,4-dioxane (4.3 ml) and 2 M aqueous sodium hydroxide solution (2.2 ml, 4.4 mmol) was stirred at room temperature for 20 h. The pH was adjusted to 2 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 (79 mg, 95%) as light brown solid. MS m/e: 193 ([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-e982c0d94e5a4b9ba240bd3aac6bf7a7
Source dataset
uspto-grants-2013_08
Patent number
US08513238B2

Reaction notes

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