Hydrochloric Acid → 2-Amino-4-[2-(hydrazinoimino-methyl)hydrazino]-butanoic acid

HRID 1109027

Reaktionsgleichung

Reaktionsgleichung von HRID 1109027
[NH2:1][C@H:2]([C:7]([OH:9])=[O:8])[CH2:3][CH2:4]ON.CS/[C:12](/[NH2:15])=[N:13]/[NH2:14].I.[N:17]#[N:18].Cl>[OH-].[Na+]>[NH2:1][CH:2]([CH2:3][CH2:4][NH:14][NH:13][CH:12]=[N:15][NH:17][NH2:18])[C:7]([OH:9])=[O:8]

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 947Nitrogen2×HCID 441443L-CanalineHCID 6508896Methyl hydrazinecarbimidothioate hydroiodide

Produkt 1

HCID 540366152-Amino-4-[2-(hydrazinoimino-methyl)hydrazino]-butanoic acid

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 14798Sodium HydroxideLösungsmittel

Reaktionsbedingungen

Temperatur
4 °C

Versuchsvorschrift

Mix canaline (2.65 g, 20 mmol) and S-methylisothiosemicarbazide hydroiodide (4.66 g, 20 mmol) in 1M NaOH (40 ml) and stir under a blanket N2 at 40° C. for 48 hours. Neutralize the reaction with 1M HCl and blow to a residue with a stream of N2. Apply the residue to a Dowex AG50-X8 column and elute with 0.2M NH4OH. Lyophilize the fractions containing the desired product and take up the resulting solid in water (20 ml). Add flavianic acid (3.2 g) in water (20 ml) and cool the solution to 4° C. for 16 hours. Filter the resulting solid and crystallize to yield the title compound.

Aufarbeitung

  1. washApply the residue to a Dowex AG50-X8 column and elute with 0.2M NH4OH
  2. additioncontaining the desired product
  3. filtrationFilter the resulting solid
  4. customcrystallize

Quellen und Nachweise

ORD-Eintrag
ord-c8cda447d7c7482da4b25906b25fe5f4
Quelldatensatz
uspto-grants-1994_06
Patentnummer
US05318992

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