Hydrochloric Acid → HCID 178525723, compound

HRID 2118254Notes

Reaction equation

HRID 2118254 reaction equation
C[O:2][C:3]([C@H:5]1[CH2:10][CH2:9][C@H:8]([CH2:11][NH:12][S:13]([C:16]2[CH:21]=[CH:20][C:19]([C:22]([F:25])([F:24])[F:23])=[CH:18][CH:17]=2)(=[O:15])=[O:14])[CH2:7][CH2:6]1)=[O:4].[OH-].[K+].Cl>CO.O>[F:25][C:22]([F:23])([F:24])[C:19]1[CH:18]=[CH:17][C:16]([S:13]([NH:12][CH2:11][C@H:8]2[CH2:7][CH2:6][C@H:5]([C:3]([OH:4])=[O:2])[CH2:10][CH2:9]2)(=[O:14])=[O:15])=[CH:21][CH:20]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 178501133HCID 178501133, compound

Product 1

HCID 178525723HCID 178525723, compoundYield 95.4%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A solution of 1.09 g (2.87 mmol) of trans-4-[(4-trifluoromethyl-benzenesulfonylamino)-methyl]-cyclohexanecarboxylic acid methyl ester and 569 mg (85%, 8.62 mmol, 3 eq) of KOH in 20 mL of MeOH and 1 mL of H2O were refluxed for 3 h. After cooling to RT, 4.5 mL of 2M aqueous HCl were added and extracted with 3 portions of 20 mL of CH2Cl2. The combined organic phases were washed with H2O, then with brine, dried over anhydrous Na2SO4 and finally evaporated, leaving 1 g (95%) of trans-4-[(4-trifluoromethyl-benzenesulfonylamino)-methyl]-cyclohexanecarboxylic acid as white solid, MS: 364 ((M−H)−).

Workup

  1. extractionextracted with 3 portions of 20 mL of CH2Cl2
  2. washThe combined organic phases were washed with H2O
  3. dry with materialwith brine, dried over anhydrous Na2SO4
  4. customfinally evaporated

Sources & evidence

ORD record
ord-2297174faafb4eb587100d97572abbe9
Source dataset
uspto-grants-2008_10
Patent number
US07442791B2

Reaction notes

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