Acetic Acid → HCID 54044520, compound

HRID 22127Notes

Reaction equation

HRID 22127 reaction equation
[NH2:1][CH2:2][CH2:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]([C:18]2[CH:19]=[N:20][CH:21]=[CH:22][CH:23]=2)=[CH:11][CH2:12][CH2:13][CH2:14][C:15]([OH:17])=[O:16])=[CH:6][CH:5]=1.C(=O)([O-])[O-].[K+].[K+].[F:30][C:31]1[CH:36]=[CH:35][C:34]([S:37](Cl)(=[O:39])=[O:38])=[CH:33][CH:32]=1.C(O)(=O)C>O1CCOCC1>[F: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]([C:10]([C:18]3[CH:19]=[N:20][CH:21]=[CH:22][CH:23]=3)=[CH: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

6

Reactant 4

HCID 176Acetic AcidHCID 95884-Fluorobenzenesulfonyl chlorideHCID 11430Potassium CarbonateHCID 54450301HCID 54450301, compound

Product 1

HCID 54044520HCID 54044520, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

3.1 g of 6-(4-(2-aminoethyl)phenyl)-6-(3-pyridyl)hex-5-enoic acid (prepared analogously to Example 10d) are stirred into 150 ml of dioxan with 5 ml of saturated potassium carbonate solution. Then 2.9 g of 4-fluorobenzenesulphonic acid chloride in 20 ml of dioxan are added and the resulting mixture is stirred overnight at ambient temperature. Acetic acid is added and a precipitate is formed. This is separated off and taken up in ethyl acetate, then dried and evaporated down. Finally, the residue is chromatographed over a silica gel column using chloroform/methanol 20:1 as eluant.

Workup

  1. customa precipitate is formed
  2. customThis is separated off
  3. customdried
  4. customevaporated down
  5. customFinally, the residue is chromatographed over a silica gel column

Sources & evidence

ORD record
ord-4423e4bef7a644369c687ff467261006
Source dataset
uspto-grants-1995_06
Patent number
US05426119

Reaction notes

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