Water → phenylmethyl 1-[N-(4-methoxybenzenesulfonyl)amino]cyclohexanecarboxylate

HRID 1953445Notes

Reaction equation

HRID 1953445 reaction equation
[NH2:1][C:2]1([C:8]([O:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[O:9])[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]1.CC1C=CC(S(O)(=O)=O)=CC=1.O.[CH3:30][O:31][C:32]1[CH:37]=[CH:36][C:35]([S:38](Cl)(=[O:40])=[O:39])=[CH:34][CH:33]=1>C(OCC)(=O)C>[CH3:30][O:31][C:32]1[CH:33]=[CH:34][C:35]([S:38]([NH:1][C:2]2([C:8]([O:10][CH2:11][C:12]3[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=3)=[O:9])[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]2)(=[O:40])=[O:39])=[CH:36][CH:37]=1

Participants

5

Reactant 3

HCID 962WaterHCID 74014-Methoxybenzenesulfonyl chlorideHCID 19763929Phenylmethyl 1-aminocyclohexanecarboxylate-p-toluenesulfonate

Product 1

HCID 23297905phenylmethyl 1-[N-(4-methoxybenzenesulfonyl)amino]cyclohexanecarboxylateYield 54%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

8.1 g (20 mmol) of phenylmethyl 1-aminocyclohexanecarboxylate ·p-toluenesulfonate was added to 50 nm of water, and then 4.1 g (20 mmol) of 4-methoxybenzenesulfonylchloride and 50 ml of ethyl acetate was added to the mixture with stirring. After stirring at room temperature, the reaction mixture was put into a separatory funnel and water layer was removed therefrom. Subsequently, organic layer was washed with successive, 10% potassium hydrogensulfate solution, and saturated brine, and then, was dried over anhydrous magnesium sulfate, and the solvent was concentrated under reduced pressure. The obtained crystal was stirred overnight in ether, whereby 4.36 g of phenylmethyl 1-[N-(4-methoxybenzenesulfonyl)amino]cyclohexanecarboxylate was obtained.

Workup

  1. stirringAfter stirring at room temperature
  2. customthe reaction mixture was put into a separatory funnel
  3. customwater layer was removed
  4. washSubsequently, organic layer was washed with successive, 10% potassium hydrogensulfate solution, and saturated brine
  5. dry with materialwas dried over anhydrous magnesium sulfate
  6. concentrationthe solvent was concentrated under reduced pressure
  7. stirringThe obtained crystal was stirred overnight in ether

Sources & evidence

ORD record
ord-c32a8e12646547849f8b7d52975ba12c
Source dataset
uspto-grants-2000_09
Patent number
US06117870

Reaction notes

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