4-Chlorobenzenesulfonyl chloride → Ethyl 3-[2-[(4-chlorophenyl)sulphonylamino]ethyl]-5-[(4-fluorophenyl)methyl]benzenepropanoate

HRID 53332Notes

Reaction equation

HRID 53332 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8](Cl)(=[O:10])=[O:9])=[CH:4][CH:3]=1.[NH2:12][CH2:13][CH2:14][C:15]1[CH:16]=[C:17]([CH2:29][CH2:30][C:31]([O:33][CH2:34][CH3:35])=[O:32])[CH:18]=[C:19]([CH2:21][C:22]2[CH:27]=[CH:26][C:25]([F:28])=[CH:24][CH:23]=2)[CH:20]=1.C(N(CC)CC)C>ClCCl>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:12][CH2:13][CH2:14][C:15]2[CH:16]=[C:17]([CH2:29][CH2:30][C:31]([O:33][CH2:34][CH3:35])=[O:32])[CH:18]=[C:19]([CH2:21][C:22]3[CH:27]=[CH:26][C:25]([F:28])=[CH:24][CH:23]=3)[CH:20]=2)(=[O:10])=[O:9])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 73984-Chlorobenzenesulfonyl chlorideHCID 8471TriethylamineHCID 19962359Ethyl 3-(2-aminoethyl)-5-[(4-fluorophenyl)methyl]benzenepropanoate

Product 1

HCID 19962373Ethyl 3-[2-[(4-chlorophenyl)sulphonylamino]ethyl]-5-[(4-fluorophenyl)methyl]benzenepropanoateYield 73.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4-chlorobenzenesulphonyl chloride (352 mg) was added portionwise to a stirred solution of ethyl 3-(2-aminoethyl)-5-[(4-fluorophenyl)methyl]benzenepropanoate (500 mg) and triethylamine (0.25 ml) in dry dichloromethane (5 ml) at room temperature. The solution was stirred at room temperature for 5 hours and then washed with water and dried (MgSO4). The solvent was evaporated and the residue was chromatographed on silica gel. Elution with dichloromethane first gave impurity followed by pure product. The product fractions were combined and evaporated to give the title compound as an oil (560 mg); Rf 0.2 (SS 3). Found: C,62.08; H,5.47; N,2.73. C26H27ClFNO4S requires C,61.96; H,5.40; N,2.78%.

Workup

  1. washwashed with water
  2. dry with materialdried (MgSO4)
  3. customThe solvent was evaporated
  4. customthe residue was chromatographed on silica gel
  5. washElution with dichloromethane first gave impurity
  6. customevaporated

Sources & evidence

ORD record
ord-ef606e518991429292a6f4369c8f085d
Source dataset
uspto-grants-1997_04
Patent number
US05618941

Reaction notes

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