2,5-Bis(2,2,2-trifluoroethoxy)benzene-1-sulfonyl chloride → HCID 178525724, compound

HRID 1984922Notes

Reaction equation

HRID 1984922 reaction equation
[NH2:1][CH2:2][C@H:3]1[CH2:8][CH2:7][C@H:6]([C:9]([OH:11])=[O:10])[CH2:5][CH2:4]1.[F:12][C:13]([F:33])([F:32])[CH2:14][O:15][C:16]1[CH:21]=[CH:20][C:19]([O:22][CH2:23][C:24]([F:27])([F:26])[F:25])=[CH:18][C:17]=1[S:28](Cl)(=[O:30])=[O:29]>C1COCC1.[OH-].[Na+]>[F:33][C:13]([F:12])([F:32])[CH2:14][O:15][C:16]1[CH:21]=[CH:20][C:19]([O:22][CH2:23][C:24]([F:25])([F:26])[F:27])=[CH:18][C:17]=1[S:28]([NH:1][CH2:2][C@H:3]1[CH2:4][CH2:5][C@H:6]([C:9]([OH:11])=[O:10])[CH2:7][CH2:8]1)(=[O:30])=[O:29]

Participants

5

Reactant 2

HCID 27360772,5-Bis(2,2,2-trifluoroethoxy)benzene-1-sulfonyl chlorideHCID 178511262HCID 178511262, compound

Product 1

HCID 178525724HCID 178525724, compoundYield 57%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 14798Sodium HydroxideSolvent

Procedure

To a solution of trans-4-aminomethyl-cyclohexanecarboxylic acid (1.5 g, 10 mmol) in THF (10 mL) and 1 M aqueous sodium hydroxide (27 mL) was added a solution of 2,5-bis(2,2,2-trifluoroethoxy)benzenesulfonyl chloride (3.8 g, 10.25 mmol) in THF (10 mL) dropwise and the mixture was stirred at ambient temperature for 2 hr. The resulting mixture was concentrated and 1 M aqueous HCl (22.5 mL) was added. The resulting precipitate was filtered, washed with water and hexanes to give trans-4-{[2,5-bis-(2,2,2-trifluoro-ethoxy)-benzenesulfonylamino]-methyl}-cyclohexanecarboxylic acid as a white powder (2.8 g, 57%).

Workup

  1. concentrationThe resulting mixture was concentrated
  2. addition1 M aqueous HCl (22.5 mL) was added
  3. filtrationThe resulting precipitate was filtered
  4. washwashed with water and hexanes

Sources & evidence

ORD record
ord-432f9903839d4efda65aa9dd235a266a
Source dataset
uspto-grants-2009_06
Patent number
US07544690B2

Reaction notes

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