Water → HCID 178524820, compound

HRID 12896Notes

Reaction equation

HRID 12896 reaction equation
C([O:3][C:4]([C:6]1[CH:7]=[N:8][N:9]([C@H:15]2[CH2:20][CH2:19][C@@H:18]([OH:21])[CH2:17][CH2:16]2)[C:10]=1[C:11]([F:14])([F:13])[F:12])=[O:5])C.[OH-].[Li+].O>CO>[OH:21][C@@H:18]1[CH2:19][CH2:20][C@H:15]([N:9]2[C:10]([C:11]([F:12])([F:13])[F:14])=[C:6]([C:4]([OH:5])=[O:3])[CH:7]=[N:8]2)[CH2:16][CH2:17]1

Participants

5

Reactant 3

HCID 962WaterHCID 3939Lithium HydroxideHCID 178470000HCID 178470000, compound

Product 1

HCID 178524820HCID 178524820, compoundYield 81.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
80 °C

Procedure

cis-1-(4-Hydroxy-cyclohexyl)-5-trifluoromethyl-1H-pyrazole-4-carboxylic acid ethyl ester (94.7 mg, 0.309 mmol) was dissolved in methanol (0.5 mL). Lithium hydroxide (10.3 mg, 0.430 mmol) and water (0.5 mL) were added and the mixture was heated at 80° C. for 1 hour. After cooling to room temperature, the methanol was removed in vacuo. Tetrahydrofuran was added and removed in vacuo to insure complete removal of methanol. The residue was diluted with water and acidified with 6N HCl (75 μL; pH 1.5-2). The solid which precipitated out of solution was collected by filtration, washed with water and dried under high vacuum at 50° C. to give cis-1-(4-hydroxy-cyclohexyl)-5-trifluoromethyl-1H-pyrazole-4-carboxylic acid (70 mg; 81%). Mass spectrum: m/z: 279.1 (M+H).

Workup

  1. temperatureAfter cooling to room temperature
  2. customthe methanol was removed in vacuo
  3. additionTetrahydrofuran was added
  4. customremoved in vacuo
  5. customremoval of methanol
  6. additionThe residue was diluted with water
  7. customThe solid which precipitated out of solution
  8. filtrationwas collected by filtration
  9. washwashed with water
  10. customdried under high vacuum at 50° C.

Sources & evidence

ORD record
ord-fdea3cbe0b1a4d8fbacfe5a4a86f90af
Source dataset
uspto-grants-2010_06
Patent number
US07728029B2

Reaction notes

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