4-Chlorobenzenesulfonyl chloride → HCID 14772689, compound

HRID 2073263Notes

Reaction equation

HRID 2073263 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]([C:17]([O:19][CH3:20])=[O:18])[CH2:13]2)(=[O:10])=[O:9])=[CH:4][CH:3]=1.C(N(CC)CC)C.[Cl:28][C:29]1[CH:34]=[CH:33][C:32]([S:35](Cl)(=[O:37])=[O:36])=[CH:31][CH:30]=1>ClCCl>[Cl:28][C:29]1[CH:34]=[CH:33][C:32]([S:35]([N:15]2[CH2:16][C@H:12]([NH:11][S:8]([C:5]3[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=3)(=[O:10])=[O:9])[CH2:13][C@H:14]2[C:17]([O:19][CH3:20])=[O:18])(=[O:37])=[O:36])=[CH:31][CH:30]=1

Participants

5

Reactant 3

HCID 73984-Chlorobenzenesulfonyl chlorideHCID 8471TriethylamineHCID 14772687HCID 14772687, compound

Product 1

HCID 14772689HCID 14772689, compoundYield 74.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (2S,4R)-4-(4-chlorophenyl-sulfonylamino)-2-methoxycarbonylpyrrolidine (10.0 g) in dichloromethane (200 ml) were added triethylamine (4.8 ml) and 4-chlorobenzenesulfonyl chloride (6.62 g) in an ice bath and the mixture was stirred in an ice bath for 3 hours. The resulting 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 to give (2S,4R)-1-(4-chlorophenylsulfonyl)-4-(4-chlorophenylsulfonylamino)-2-methoxycarbonylpyrrolidine (11.5 g).

Workup

  1. washThe resulting solution was washed successively with diluted hydrochloric acid, saturated aqueous sodium bicarbonate and brine
  2. dry with materialdried over magnesium sulfate
  3. customThe solvent was evaporated in vacuo

Sources & evidence

ORD record
ord-d00f7f43daf24fdfa569273b1361a78f
Source dataset
uspto-grants-1990_04
Patent number
US04916152

Reaction notes

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