Diethylenetriamine → tert-butyl N-{2-[(2-{[(tert-butoxy)carbonyl]amino}ethyl)amino]ethyl}carbamate

HRID 505007Notes

Reaction equation

[NH2:1][CH2:2][CH2:3][NH:4][CH2:5][CH2:6][NH2:7].[C:8]([O:12][C:13]([O:15]N=C(C1C=CC=CC=1)C#N)=O)([CH3:11])([CH3:10])[CH3:9]>O1CCCC1>[C:8]([O:12][C:13]([NH:1][CH2:2][CH2:3][NH:4][CH2:5][CH2:6][NH:7][C:13]([O:12][C:8]([CH3:9])([CH3:10])[CH3:11])=[O:15])=[O:15])([CH3:11])([CH3:10])[CH3:9]

Participants

Conditions

Temperature: 0 °C

Procedure

A solution of diethylenetriamine (0.42 g; 4.1 mmol) in tetrahydrofuran (THF; 5 ml) is stirred at 0° C. under nitrogen for 20 minutes. A solution of 2-(tert-butoxycarbonyloximino)-2-phenylacetonitrile (Boc-ON; 2.04 g; 8.2 mmol) in THF (5 ml) is then added dropwise and the reaction mixture is stirred at 0° C. for 1 hour. The solvent is eliminated at reduced pressure and the resulting residue is purified by silica gel column chromatography with methanol-ammonium hydroxide 100:3. 1.2 g (yield 96%) of an oil having the following characteristics is thus obtained:

Workup

customthe resulting residue is purified by silica gel column chromatography with methanol-ammonium hydroxide 100:3

Sources & evidence

ORD record: ord-c4e442d740cb4b349ff890724536c87d
Source dataset: uspto-grants-2010_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07781417B2

Reaction notes

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