4-Chlorobenzenesulfonyl chloride → Trans-2-(4-Chloro-benzenesulfonylamino)-cyclohexanecarboxylic acid

HRID 990913Notes

Reaction equation

HRID 990913 reaction equation
[NH2:1][C@@H:2]1[CH2:7][CH2:6][CH2:5][CH2:4][C@H:3]1[C:8]([OH:10])=[O:9].[OH-].[Na+].[Cl:13][C:14]1[CH:19]=[CH:18][C:17]([S:20](Cl)(=[O:22])=[O:21])=[CH:16][CH:15]=1>O.C1(C)C=CC=CC=1>[Cl:13][C:14]1[CH:19]=[CH:18][C:17]([S:20]([NH:1][C@@H:2]2[CH2:7][CH2:6][CH2:5][CH2:4][C@H:3]2[C:8]([OH:10])=[O:9])(=[O:22])=[O:21])=[CH:16][CH:15]=1

Participants

6

Reactant 3

HCID 73984-Chlorobenzenesulfonyl chlorideHCID 14798Sodium HydroxideHCID 2724640trans-2-Aminocyclohexanecarboxylic acid

Product 1

HCID 69656371Trans-2-(4-Chloro-benzenesulfonylamino)-cyclohexanecarboxylic acid

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 1140TolueneSolvent2×

Procedure

Trans-2-Aminocyclohexanecarboxylic acid (0.150 g, 1.05 mmol) is dissolved in 1.5 ml of water and NaOH (0.09 g, 2.25 mmol) in 1.5 ml of water is added at 0° C. 4-Chlorobenzene sulfonyl chloride (0.243 g, 1.15 mmol) in 1.5 ml of toluene is added. The reaction mixture is stirred at room temperature for 16 hours. The toluene layer is separated and the aqueous layer is washed twice with toluene. The toluene layers are discarded. Ethyl acetate is added to the aqueous layer (15 ml) and 2M HCl until pH<7. The two phases are separated and the aqueous layer is extracted with ethyl acetate (3×15 mL). The combined organic phases are washed with brine (20 ml), dried over MgSO4 and the ethyl acetate is removed under reduced pressure leaving a white solid that is dissolved in toluene (2×10 ml) and concentrated .The product is dried in vacuum.

Workup

  1. customThe toluene layer is separated
  2. washthe aqueous layer is washed twice with toluene
  3. additionEthyl acetate is added to the aqueous layer (15 ml) and 2M HCl until pH<7
  4. customThe two phases are separated
  5. extractionthe aqueous layer is extracted with ethyl acetate (3×15 mL)
  6. washThe combined organic phases are washed with brine (20 ml)
  7. dry with materialdried over MgSO4
  8. customthe ethyl acetate is removed under reduced pressure
  9. customleaving a white solid
  10. concentrationconcentrated .The product
  11. customis dried in vacuum

Sources & evidence

ORD record
ord-224e6608a24646f287f328614ec6fe80
Source dataset
uspto-grants-2002_10
Patent number
US06462076B2

Reaction notes

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