N-BOC-ethylenediamine → n-Boc-2-aminoethylguanidine hydroiodide

HRID 566866

Reaktionsgleichung

Reaktionsgleichung von HRID 566866
[C:1]([NH:8][CH2:9][CH2:10][NH2:11])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[IH:12].CS[C:15](=[NH:17])[NH2:16]>C(O)C>[IH:12].[C:1]([N:8]([CH2:9][CH2:10][NH2:11])[C:15]([NH2:17])=[NH:16])([O:3][C:4]([CH3:5])([CH3:6])[CH3:7])=[O:2]

Komponenten

4

Edukt 2

HCID 187201N-BOC-ethylenediamineHCID 197812S-methylthiouronium iodide

Produkt 1

HCID 23513565n-Boc-2-aminoethylguanidine hydroiodideAusbeute 72,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

A solution of commercial N-BOC-ethylendiamine (1 g) in dry ethanol (100 ml) and 2-methyl-2-thiopseudourea hydroiodide (1.5 g) was refluxed for 8 hours. The solvent was removed at reduced pressure and the crude residue purified by flash chromatography (methylene chloride/methanol: 9/1) to yield 1.5 g of N-BOC-2-aminoethylguanidine hydroiodide as a yellow oil which was dissolved in methanolic hydrochloric acid solution 5N (20 ml) and stirred at room temperature for 3 hours. The white precipitate was collected, washed with dry ethanol, affording 700 mg of the intermediate.

Aufarbeitung

  1. customThe solvent was removed at reduced pressure
  2. customthe crude residue purified by flash chromatography (methylene chloride/methanol: 9/1)

Quellen und Nachweise

ORD-Eintrag
ord-5e8fdbaf74cb42bbb3395e3e14e0ff94
Quelldatensatz
uspto-grants-2001_01
Patentnummer
US06177408B1

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