Hydrochloric Acid → Octamoxin

HRID 566321

Reaktionsgleichung

Reaktionsgleichung von HRID 566321
[CH3:1][C:2](=[N:9][NH:10]C(OC(C)(C)C)=O)[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].C([BH3-])#N.[Na+].Cl.[OH-].[Na+]>C1COCC1.CO>[CH3:1][CH:2]([NH:9][NH2:10])[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8]

Komponenten

7

Edukt 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 5003444Sodium cyanoborohydrideHCID 72599198tert-Butyl N'-(1-methyl-heptylidene)-hydrazinecarboxylate

Produkt 1

HCID 20811Octamoxin

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

74.08 g (305.7 mmol) of tert-butyl N′-(1-methyl-heptylidene)-hydrazinecarboxylate are dissolved in a mixture of 235 ml of THF and 310 ml of methanol and, after 22.34 g (354.6 mmol) of sodium cyanoborohydride have been added, the mixture is stirred for 1 hour at room temperature. 213 ml of 6N HCl are added dropwise and, after the addition has ended, the mixture is refluxed for 1.5 hours. It is neutralized with 6N NaOH solution, then, after the non-aqueous solvents have been removed, extracted three times with dichloromethane, and, after the mixture has been dried over sodium sulphate, the solvent is removed in vacuo. This gives 37.5 g (85%) of a yellow oil.

Aufarbeitung

  1. additionafter the addition
  2. temperaturethe mixture is refluxed for 1.5 hours
  3. customafter the non-aqueous solvents have been removed
  4. extractionextracted three times with dichloromethane
  5. dry with materialafter the mixture has been dried over sodium sulphate
  6. customthe solvent is removed in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-9bb64b2018d74f30935863ff29605f87
Quelldatensatz
uspto-grants-2001_01
Patentnummer
US06174884B1

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