Hydrochloric Acid → Potassium 8-(p-chlorophenylsulfonamido)-4-[3-(3-pyridyl)-2-propenyl]octanoate

HRID 1494105Notes

Reaction equation

HRID 1494105 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][CH2:12][CH2:13][CH2:14][CH2:15][CH:16]([CH2:23][CH:24]=[CH:25][C:26]2[CH:27]=[N:28][CH:29]=[CH:30][CH:31]=2)[CH2:17][CH2:18][C:19]([O:21]C)=[O:20])(=[O:10])=[O:9])=[CH:4][CH:3]=1.Cl.CC(C)([O-])C.[K+:38]>O1CCOCC1.[OH-].[Na+].C(O)(C)(C)C.O1CCCC1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([S:8]([NH:11][CH2:12][CH2:13][CH2:14][CH2:15][CH:16]([CH2:23][CH:24]=[CH:25][C:26]2[CH:27]=[N:28][CH:29]=[CH:30][CH:31]=2)[CH2:17][CH2:18][C:19]([O-:21])=[O:20])(=[O:9])=[O:10])=[CH:6][CH:7]=1.[K+:38]

Participants

8

Reactant 3

HCID 313Hydrochloric AcidHCID 23665647Potassium tert-butoxideHCID 54073742Methyl 8-(p-chlorophenylsulfonamido)-4-[3-(3-pyridyl)-2-propenyl]octanoate

Product 1

HCID 67916594Potassium 8-(p-chlorophenylsulfonamido)-4-[3-(3-pyridyl)-2-propenyl]octanoate

Reagents, catalysts & solvents 4

HCID 6386tert-ButanolSolventHCID 8028TetrahydrofuranSolventHCID 14798Sodium HydroxideSolventHCID 312751,4-DioxaneSolvent

Procedure

A mixture of 0.097 g of methyl 8-(p-chlorophenylsulfonamido)-4-[3-(3-pyridyl)-2-propenyl]octanoate in 1 mL dioxane and 0.45 mL 1N sodium hydroxide is stirred at room temperature for 18 hours. The mixture is acidified with 0.45 mL of 1N hydrochloric acid and then subjected to evaporation. The residue is triturated with methylene chloride and the organic phase is dried, filtered and evaporated to yield a light amber oil. The oil is dissolved in 1 mL t-butanol and one equivalent of potassium t-butoxide in tetrahydrofuran is added. The mixture is freeze-dried to obtain potassium 8-(p-chlorophenylsulfonamido)-4-[3-(3-pyridyl)-2-propenyl]octanoate as about a 1:1 mixture of cis and trans isomers.

Workup

  1. customsubjected to evaporation
  2. customThe residue is triturated with methylene chloride
  3. customthe organic phase is dried
  4. filtrationfiltered
  5. customevaporated
  6. customto yield a light amber oil
  7. customThe mixture is freeze-dried

Sources & evidence

ORD record
ord-1e7de318b8c34b9aac3b9f27dd4bcc80
Source dataset
uspto-grants-1991_06
Patent number
US05025025

Reaction notes

Loading…