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

HRID 1494105Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1494105
[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]

Komponenten

8

Edukt 3

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 6386tert-ButanolLösungsmittelHCID 8028TetrahydrofuranLösungsmittelHCID 14798Sodium HydroxideLösungsmittelHCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-1e7de318b8c34b9aac3b9f27dd4bcc80
Quelldatensatz
uspto-grants-1991_06
Patentnummer
US05025025

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