Hydrochloric Acid → HCID 178434086, compound

HRID 1893369Notes

Reaction equation

HRID 1893369 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])=[C:15]([CH3:18])[C:14]([CH3:19])=[N:13]2)[CH2:8][CH2:7]1)=[O:5])C.[OH-].[Na+].Cl>O1CCOCC1>[CH3:19][C:14]1[C:15]([CH3:18])=[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 178472401HCID 178472401, compound

Product 1

HCID 178434086HCID 178434086, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A solution of trans-4-(3,4,5-trimethyl-pyrazol-1-yl)-cyclohexanecarboxylic acid ethyl ester (180 mg, 0.681 mmol) in 1,4-dioxane (6.8 ml) and 2 M aqueous sodium hydroxide solution (3.4 ml, 6.8 mmol) was stirred at room temperature for 3 days. 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 (141 mg, 88%) as light brown solid. MS m/e: 235 ([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-0613a5c70dd846e98824a040fa9a6491
Source dataset
uspto-grants-2013_08
Patent number
US08513238B2

Reaction notes

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