Lithium Hydroxide → HCID 58117255, compound

HRID 1406424Notes

Reaction equation

HRID 1406424 reaction equation
C([O:3][C:4]([C:6]1[CH:7]=[N:8][N:9]([C@H:11]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH3:12])[CH:10]=1)=[O:5])C.[OH-].[Li+]>O1CCCC1.O>[C:13]1([C@@H:11]([N:9]2[CH:10]=[C:6]([C:4]([OH:5])=[O:3])[CH:7]=[N:8]2)[CH3:12])[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 58117375HCID 58117375, compound

Product 1

HCID 58117255HCID 58117255, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Intermediate (6f), 1-((S)-1-Phenyl-ethyl)-1H-pyrazole-4-carboxylic acid ethyl ester (1.525 g, 6.2 mmol) was stirred in a mixture of tetrahydrofuran (20 mL) and water (20 mL). Lithium hydroxide (0.524 g, 12.5 mmol) was added and the reaction stirred at ambient temperature for 24 hours. The reaction mixture was reduced in volume and extracted with diethyl ether (3×20 mL). The aqueous layer was carefully acidified using an aqueous 6N hydrochloric acid solution. The resulting precipitate was filtered, washed with copious amounts of water and dried in vacuo to afford intermediate (6g), 1-((S)-1-Phenyl-ethyl)-1H-pyrazole-4-carboxylic acid as a white solid, 0.664 g, 49%.

Workup

  1. extractionextracted with diethyl ether (3×20 mL)
  2. filtrationThe resulting precipitate was filtered
  3. washwashed with copious amounts of water
  4. customdried in vacuo

Sources & evidence

ORD record
ord-bc8ad45591ab445684ae341ba89d069e
Source dataset
uspto-grants-2014_12
Patent number
US08916591B2

Reaction notes

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