4-Chlorobenzenesulfonyl chloride → HCID 10343879, compound

HRID 465526Notes

Reaction equation

HRID 465526 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][CH:5]([CH2:13][CH2:14][C:15]1[CH:16]=[N:17][CH:18]=[CH:19][CH:20]=1)[CH2:6][CH2:7][CH2:8][C:9]([O:11][CH3:12])=[O:10].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>C(Cl)Cl.CN(C)C1C=CN=CC=1>[Cl:28][C:29]1[CH:34]=[CH:33][C:32]([S:35]([NH:1][CH2:2][CH2:3][CH2:4][CH:5]([CH2:13][CH2:14][C:15]2[CH:16]=[N:17][CH:18]=[CH:19][CH:20]=2)[CH2:6][CH2:7][CH2:8][C:9]([O:11][CH3:12])=[O:10])(=[O:37])=[O:36])=[CH:31][CH:30]=1

Participants

6

Reactant 3

HCID 73984-Chlorobenzenesulfonyl chlorideHCID 8471TriethylamineHCID 10107615HCID 10107615, compound

Product 1

HCID 10343879HCID 10343879, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 0.127 g (9.045 mmol) of methyl 8-amino-5-[2-(3-pyridyl)ethyl]-octanoate in 5 ml methylene chloride are added a few crystals of 4-dimethylaminopyridine followed by 0.1 ml (0.7 mmol) triethylamine and 0.112 g p-chlorophenylsulfonyl chloride, and the solution is stirred at room temperature for 16 h. The reaction mixture is diluted with 10 ml methylene chloride and washed with saturated aqueous sodium bicarbonate solution. The organic phase is dried (MgSO4), filtered and evaporated to obtain an oil which is purified by preparative thin layer chromatography to give methyl 8-(p-chlorophenylsulfonamido)-5-[2-(3-pyridyl)ethyl]-octanoate as an oil.

Workup

  1. washwashed with saturated aqueous sodium bicarbonate solution
  2. dry with materialThe organic phase is dried (MgSO4)
  3. filtrationfiltered
  4. customevaporated
  5. customto obtain an oil which
  6. customis purified by preparative thin layer chromatography

Sources & evidence

ORD record
ord-734e92fde618477890f311a33ac08c1c
Source dataset
uspto-grants-1992_10
Patent number
US05153214

Reaction notes

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