4-Chlorobenzenesulfonyl chloride → 1-(4-Chlorophenylsulfonyl)-4-(4-chlorophenylsulfonylamino) pyrrolidine

HRID 2073257Notes

Reaction equation

HRID 2073257 reaction equation
FC(F)(F)C(O)=O.[Cl:8][C:9]1[CH:14]=[CH:13][C:12]([S:15]([NH:18][CH:19]2[CH2:23][NH:22][CH2:21][CH2:20]2)(=[O:17])=[O:16])=[CH:11][CH:10]=1.C(N(CC)CC)C.[Cl:31][C:32]1[CH:37]=[CH:36][C:35]([S:38](Cl)(=[O:40])=[O:39])=[CH:34][CH:33]=1>ClCCl>[Cl:31][C:32]1[CH:37]=[CH:36][C:35]([S:38]([N:22]2[CH2:23][CH:19]([NH:18][S:15]([C:12]3[CH:11]=[CH:10][C:9]([Cl:8])=[CH:14][CH:13]=3)(=[O:17])=[O:16])[CH2:20][CH2:21]2)(=[O:40])=[O:39])=[CH:34][CH:33]=1

Participants

5

Reactant 3

HCID 73984-Chlorobenzenesulfonyl chlorideHCID 8471TriethylamineHCID 867438494-(4-Chlorophenylsulfonylamino)pyrrolidine trifluoroacetate

Product 1

HCID 177669441-(4-Chlorophenylsulfonyl)-4-(4-chlorophenylsulfonylamino) pyrrolidineYield 28.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (2S,4R)-2-[(E and Z)-5-carboxy-1-pentenyl]-4-(4-chlorophenylsulfonylamino)pyrrolidine trifluoroacetate (7.85 g) in dichloromethane (80 ml) were added triethylamine (8.98 ml) and 4-chlorobenzenesulfonyl chloride (3.40 g) under an ice bath cooling and the mixture was stirred at the same temperature for 1.5 hours. The solution was washed successively with diluted hydrochloric acid and water and the organic phase was extracted with 1N aqueous sodium hydroxide. The aqueous phase was washed with ethyl acetate and adjusted to pH 3 with 3N hydrochloric acid. The aqueous solution was extracted with ethyl acetate and the organic phase was washed successively with water and brine and dried over magnesium sulfate. The solvent was evaporated in vacuo and the residue was chromatographed on a silica gel column with chloroform as an eluent to give (2S,4R)-2-[(E and Z)-5-carboxy-1-pentenyl]-1-(4-chlorophenylsulfonyl)-4-(4-chlorophenylsulfonylamino) pyrrolidine (2.03 g) as a pale yellow crystal.

Workup

  1. temperaturecooling
  2. washThe solution was washed successively with diluted hydrochloric acid and water
  3. extractionthe organic phase was extracted with 1N aqueous sodium hydroxide
  4. washThe aqueous phase was washed with ethyl acetate
  5. extractionThe aqueous solution was extracted with ethyl acetate
  6. washthe organic phase was washed successively with water and brine
  7. dry with materialdried over magnesium sulfate
  8. customThe solvent was evaporated in vacuo
  9. customthe residue was chromatographed on a silica gel column with chloroform as an eluent

Sources & evidence

ORD record
ord-b4685c01c61e47b8a12d2e9f903cc851
Source dataset
uspto-grants-1990_04
Patent number
US04916152

Reaction notes

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