4-Chlorobenzenesulfonyl chloride → HCID 67863379, compound

HRID 2073259Notes

Reaction equation

HRID 2073259 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][C@H:12]2[CH2:16][NH:15][C@H:14](/[CH:17]=[CH:18]\[C:19]3[CH:24]=[CH:23][C:22]([C:25]([O:27][CH3:28])=[O:26])=[CH:21][CH:20]=3)[CH2:13]2)(=[O:10])=[O:9])=[CH:4][CH:3]=1.C(N(CC)CC)C.[Cl:36][C:37]1[CH:42]=[CH:41][C:40]([S:43](Cl)(=[O:45])=[O:44])=[CH:39][CH:38]=1>ClCCl>[Cl:36][C:37]1[CH:42]=[CH:41][C:40]([S:43]([N:15]2[CH2:16][C@H:12]([NH:11][S:8]([C:5]3[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=3)(=[O:9])=[O:10])[CH2:13][C@H:14]2/[CH:17]=[CH:18]\[C:19]2[CH:20]=[CH:21][C:22]([C:25]([O:27][CH3:28])=[O:26])=[CH:23][CH:24]=2)(=[O:45])=[O:44])=[CH:39][CH:38]=1

Participants

5

Reactant 3

HCID 73984-Chlorobenzenesulfonyl chlorideHCID 8471TriethylamineHCID 15670382HCID 15670382, compound

Product 1

HCID 67863379HCID 67863379, compoundYield 96.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a suspension of (2S,4R)-4-(4-chlorophenyl-sulfonylamino)-2-[(Z)-2-(4-methoxycarbonylphenyl)vinyl]pyrrolidine (11.5 g) in dichloromethane (200 ml) were added triethylamine (3.80 ml) and 4-chlorobenzenesulfonyl chloride (5.77 g) under ice bath cooling and the mixture was stirred at room temperature for 1 hour. The solution was washed successively with diluted hydrochloric acid, saturated aqueous sodium bicarbonate and brine and dried over magnesium sulfate. The solvent was evaporated in vacuo and the residual solid was collected by filtration to give (2S,4R)-1-(4-chlorophenylsulfonyl)-4-(4-chlorophenylsulfonylamino)-2-[(Z)-2-(4-methoxycarbonylphenyl)vinyl]pyrrolidine (15.71 g) as a white powder

Workup

  1. temperaturecooling
  2. washThe solution was washed successively with diluted hydrochloric acid, saturated aqueous sodium bicarbonate and brine
  3. dry with materialdried over magnesium sulfate
  4. customThe solvent was evaporated in vacuo
  5. filtrationthe residual solid was collected by filtration

Sources & evidence

ORD record
ord-7341c31f5ac1463caa535987df47aaa8
Source dataset
uspto-grants-1990_04
Patent number
US04916152

Reaction notes

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