4-Chlorobenzenesulfonyl chloride → Methyl [2-[(4-chlorophenyl)sulfonylamino]indan-5-yl]acetate

HRID 1612889Notes

Reaction equation

HRID 1612889 reaction equation
[NH2:1][CH:2]1[CH2:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([CH2:11][C:12]([O:14][CH3:15])=[O:13])[CH:8]=2)[CH2:3]1.C([C@@](C(O)=O)(O)[C@@](C(=O)C1C=CC=CC=1)(O)C(O)=O)(=O)C1C=CC=CC=1.C(=O)([O-])[O-].[K+].[K+].[Cl:48][C:49]1[CH:54]=[CH:53][C:52]([S:55](Cl)(=[O:57])=[O:56])=[CH:51][CH:50]=1>C(OCC)(=O)C.O>[Cl:48][C:49]1[CH:54]=[CH:53][C:52]([S:55]([NH:1][CH:2]2[CH2:10][C:9]3[C:4](=[CH:5][CH:6]=[C:7]([CH2:11][C:12]([O:14][CH3:15])=[O:13])[CH:8]=3)[CH2:3]2)(=[O:57])=[O:56])=[CH:51][CH:50]=1

Participants

7

Reactant 4

HCID 73984-Chlorobenzenesulfonyl chlorideHCID 11430Potassium CarbonateHCID 12362976dibenzoyl-L(+)tartaric acidHCID 14071505Methyl (-)-(2-aminoindan-5-yl)acetate

Product 1

HCID 53769737Methyl [2-[(4-chlorophenyl)sulfonylamino]indan-5-yl]acetate

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

Methyl (-)-(2-aminoindan-5-yl)acetate.(-)-dibenzoyl-L-tartaric acid salt (3.94 g) is added to a mixture of potassium carbonate (4.83 g), water (50 ml) and ethyl acetate (70 ml), and 4-chlorophenylsulfonyl chloride (1.49 g) is added thereto. The mixture is stirred at room temperature for one hour. The ethyl acetate layer is separated from the reaction mixture, washed with an aqueous sodium hydrogen carbonate solution, dried, and distilled under reduced pressure to remove the solvent. The residue is recrystallized from a mixture of ethyl acetate and hexane to give methyl (-)-[2-[(4-chlorophenyl)sulfonylamino]indan-5-yl]acetate (2.43 g) as colorless crystals.

Workup

  1. additionis added
  2. customThe ethyl acetate layer is separated from the reaction mixture
  3. washwashed with an aqueous sodium hydrogen carbonate solution
  4. customdried
  5. distillationdistilled under reduced pressure
  6. customto remove the solvent
  7. customThe residue is recrystallized from a mixture of ethyl acetate and hexane

Sources & evidence

ORD record
ord-d6c2b9cd1bfa429bbaf820c3a4053798
Source dataset
uspto-grants-1993_03
Patent number
US05190975

Reaction notes

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