17-Azido-3,6,9,12,15-pentaoxaheptadecan-1-amine synthesis

8synthesis methods

Product Name:17-Azido-3,6,9,12,15-pentaoxaheptadecan-1-amine
CAS Number:516493-93-9
Molecular formula:C12H26N4O5
Molecular Weight:306.36

3,6,9,12,15-PENTAOXAHEPTADECANE-1,17-DIYL BIS-AZIDE

356046-26-9
54 suppliers
$90.00/1g

17-Azido-3,6,9,12,15-pentaoxaheptadecan-1-amine

516493-93-9
112 suppliers
$29.00/250mg

Yield: 95%

Reaction Conditions:

with hydrogenchloride;triphenylphosphine in diethyl ether;water at 20; for 4 h;

Steps:

b
To a vigorously stirred suspension of l,17-diazido-3,6,9,12,15-pentaoxaheptadecane (25 g, 75 mmol) in 5 % HCl (200 mL) was added a solution of triphenylphosphine (19.2 g, 73 mmol) in ether (150 mL) over 3 hrs at room temperature. The reaction mixture was stirred for additional 24 hrs. The phases were separated and the aqueous phase was extracted with dichloromethane (3 x 40 mL). The aqueous phase was cooled in an ice/water bath and the pH was adjusted to 12 by addition of solid potassium hydroxide. The aqueous phase was concentrated and the product was taken up in dichloromethane (150 mL). The organic phase was dried (Na₂SO₄) and concentrated giving of 22 g (95 %) of a yellow oil. The product was identified by elctrospray mass spectrometry (ESI-MS) (MH⁺ calculated: 307.19; found 307.4). The crude oil was used in the nest step without further purification.

References:

GE HEALTHCARE AS WO2008/72976, 2008, A2 Location in patent:Page/Page column 22