4-Chlorobenzenesulfonyl chloride → HCID 10458455, compound

HRID 465537Notes

Reaction equation

HRID 465537 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH:7]([CH2:14][CH2:15][CH2:16][CH2:17][C:18]1[CH:19]=[N:20][CH:21]=[CH:22][CH:23]=1)[CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10].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>C(Cl)Cl>[Cl:31][C:32]1[CH:37]=[CH:36][C:35]([S:38]([NH:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH:7]([CH2:14][CH2:15][CH2:16][CH2:17][C:18]2[CH:19]=[N:20][CH:21]=[CH:22][CH:23]=2)[CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10])(=[O:40])=[O:39])=[CH:34][CH:33]=1

Participants

5

Reactant 3

HCID 73984-Chlorobenzenesulfonyl chlorideHCID 8471TriethylamineHCID 10245475HCID 10245475, compound

Product 1

HCID 10458455HCID 10458455, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 1.0 g of ethyl 8-amino-3-[4-(3-pyridyl)-butyl]-octanoate in 100 ml of methylene chloride is added 3 g of triethylamine followed by the dropwise addition of a solution of 1.5 g of p-chlorophenylsulfonyl chloride in 15 ml of methylene chloride. The reaction mixture is concentrated then directly purified by chromatography on silica gel using 25% ethyl acetate in methylene chloride as eluent to yield ethyl 8-(p-chlorophenylsulfonamido)-3-[4-(3-pyridyl)-butyl]-octanoate.

Workup

  1. concentrationThe reaction mixture is concentrated
  2. customthen directly purified by chromatography on silica gel using 25% ethyl acetate in methylene chloride as eluent

Sources & evidence

ORD record
ord-ec80461f8b4e4020b1799d187e532622
Source dataset
uspto-grants-1992_10
Patent number
US05153214

Reaction notes

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