Hydrochloric Acid → 7-[Carbamoyl(4-hydroxynonyl)amino]heptanoic acid

HRID 1729912Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1729912
[OH-:1].[Na+].[OH:3][CH:4]([CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])[CH2:5][CH2:6][CH2:7][N:8]([CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][C:17]([OH:19])=[O:18])[C:9]#[N:10].OO.Cl>O.C(O)C>[OH:3][CH:4]([CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])[CH2:5][CH2:6][CH2:7][N:8]([CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][C:17]([OH:19])=[O:18])[C:9]([NH2:10])=[O:1]

Komponenten

7

Edukt 4

HCID 313Hydrochloric AcidHCID 784Hydrogen PeroxideHCID 14798Sodium HydroxideHCID 714447027-[Cyano(4-hydroxynonyl)amino]heptanoic acid

Produkt 1

HCID 215014417-[Carbamoyl(4-hydroxynonyl)amino]heptanoic acid

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittelHCID 962WaterLösungsmittel2×

Versuchsvorschrift

To a solution of sodium hydroxide (0.4 g., excess) in water (50 ml.) and ethanol (50 ml.) is added 7-[N-(4-hydroxynonyl)cyanamido]heptanoic acid (1.5 g., 0.005 mole). The clear solution that is obtained is treated with 30% hydrogen peroxide (1.25 ml., excess). At the end of two hours the reaction mixture is poured into water (150 ml.), acidified with hydrochloric acid (dil.) and extracted with methylene chloride (3 × 75 ml.). The organic layer is washed with brine then dried over sodium sulfate. Evaporation of the solvent affords an oil which becomes solid on standing. The solid is crystallized from butyl chloride to give 7-[1-(4-hydroxynonyl)ureido]heptanoic acid. The yield is 1.4 g. (85%) of natural melting at 75°-76° C.

Aufarbeitung

  1. customThe clear solution that is obtained
  2. extractionextracted with methylene chloride (3 × 75 ml.)
  3. washThe organic layer is washed with brine
  4. dry with materialthen dried over sodium sulfate
  5. customEvaporation of the solvent
  6. customaffords an oil which
  7. customThe solid is crystallized from butyl chloride

Quellen und Nachweise

ORD-Eintrag
ord-a1eb22f700484ec48f6a51e58f0a2cd0
Quelldatensatz
uspto-grants-1976_11
Patentnummer
US03989749

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