Acetic Anhydride → HCID 21401618, Verbindung

HRID 973199Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 973199
[OH:1][CH:2]([CH2:11][O:12][C:13]1[CH:18]=[CH:17][C:16]([F:19])=[CH:15][CH:14]=1)[CH2:3][CH2:4][CH2:5][NH:6][S:7]([CH3:10])(=[O:9])=[O:8].C([O:23][C:24](=[O:26])[CH3:25])(=O)C>C(OCC)C>[C:2]([O:1][CH:2]([CH2:11][O:12][C:13]1[CH:14]=[CH:15][C:16]([F:19])=[CH:17][CH:18]=1)[CH2:3][CH2:4][CH2:5][N:6]([CH2:15][CH2:14][CH2:13][CH2:18][CH2:17][CH2:25][C:24]([OH:23])=[O:26])[S:7]([CH3:10])(=[O:9])=[O:8])(=[O:1])[CH3:3]

Komponenten

4

Edukt 2

HCID 7918Acetic AnhydrideHCID 86735163N-[4-Hydroxy-5-(4-fluorophenoxy)pentyl]-methanesulfonamide

Produkt 1

HCID 21401618HCID 21401618, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3283Diethyl EtherLösungsmittel

Versuchsvorschrift

A mixture of 7-{N-[4-hydroxy-45-(4-fluorophenoxy)- pentyl]methanesulfonamido}heptanoic acid (12.3 g., 0.03 mole) (Example 1, Step E) and acetic anhydride (6.1 g., 0.06 mole) is kept at room temperature for 18 hours. This mixture is taken up in 80 ml. of ethyl ether. The solution is extracted with an ice-cold solution of 8 g. of sodium hydroxide in 150 ml. of water. The basic solution is separated and acidified with concentrated hydrochloric acid. The crude product that separates is extracted into ether, washed with water and dried over sodium sulfate. The ether is evaporated and the residual oil is purified by chromatography on silica gel using 2% methanol in chloroform as the eluting solvent. There is obtained 7-{N-[4- acetoxy-5-(4-fluorophenoxy)pentyl]methanesulfonamido}- heptanoic acid as a viscous oil.

Aufarbeitung

  1. extractionThe solution is extracted with an ice-cold solution of 8 g
  2. customThe basic solution is separated
  3. extractionThe crude product that separates is extracted into ether
  4. washwashed with water
  5. dry with materialdried over sodium sulfate
  6. customThe ether is evaporated
  7. customthe residual oil is purified by chromatography on silica gel using 2% methanol in chloroform as the eluting solvent

Quellen und Nachweise

ORD-Eintrag
ord-38c1fdb879ac43e9a0c3bb65961a26c9
Quelldatensatz
uspto-grants-1977_10
Patentnummer
US04055596

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