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

HRID 566866Notes

Reaction equation

HRID 566866 reaction equation
[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]

Participants

4

Reactant 2

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

Product 1

HCID 23513565n-Boc-2-aminoethylguanidine hydroiodideYield 72.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

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.

Workup

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

Sources & evidence

ORD record
ord-5e8fdbaf74cb42bbb3395e3e14e0ff94
Source dataset
uspto-grants-2001_01
Patent number
US06177408B1

Reaction notes

Loading…