4-Chlorobenzenesulfonyl chloride → 6-(4-(2-((4-Chlorobenzene-1-sulfonyl)amino)ethyl)phenyl)-6-(pyridin-3-yl)hexanoic acid

HRID 22116Notes

Reaction equation

HRID 22116 reaction equation
[NH2:1][CH2:2][CH2:3][C:4]1[CH:9]=[CH:8][C:7]([CH:10]([C:18]2[CH:19]=[N:20][CH:21]=[CH:22][CH:23]=2)[CH2:11][CH2:12][CH2:13][CH2:14][C:15]([OH:17])=[O:16])=[CH:6][CH:5]=1.C(=O)([O-])[O-].[K+].[K+].[Cl:30][C:31]1[CH:36]=[CH:35][C:34]([S:37](Cl)(=[O:39])=[O:38])=[CH:33][CH:32]=1>O1CCOCC1>[Cl:30][C:31]1[CH:36]=[CH:35][C:34]([S:37]([NH:1][CH2:2][CH2:3][C:4]2[CH:5]=[CH:6][C:7]([CH:10]([C:18]3[CH:19]=[N:20][CH:21]=[CH:22][CH:23]=3)[CH2:11][CH2:12][CH2:13][CH2:14][C:15]([OH:17])=[O:16])=[CH:8][CH:9]=2)(=[O:39])=[O:38])=[CH:33][CH:32]=1

Participants

5

Reactant 3

HCID 73984-Chlorobenzenesulfonyl chlorideHCID 11430Potassium CarbonateHCID 15057040HCID 15057040, compound

Product 1

HCID 30770036-(4-(2-((4-Chlorobenzene-1-sulfonyl)amino)ethyl)phenyl)-6-(pyridin-3-yl)hexanoic acid

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

1.9 g of 6-(4-(2-aminoethyl)phenyl)-6-(3-pyridyl)hexanoic acid are suspended in 150 ml of dioxan and 20 ml of 5% potassium carbonate solution are added thereto. 1.54 g of 4-chlorobenzenesulphonic acid chloride in 20 ml of dioxan are added to this mixture at ambient temperature. After 5 hours it is rotary evaporated to dryness, the residue is taken up in a little sodium hydroxide solution and then precipitated with dilute acetic acid. The precipitate is collected, dried and then chromatographed over a silica gel column using chloroform/methanol (10:1) as eluant.

Workup

  1. customAfter 5 hours it is rotary evaporated to dryness
  2. customprecipitated with dilute acetic acid
  3. customThe precipitate is collected
  4. customdried
  5. customchromatographed over a silica gel column

Sources & evidence

ORD record
ord-718e764ddcbc489d8c83cd5580b429c5
Source dataset
uspto-grants-1995_06
Patent number
US05426119

Reaction notes

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