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ChemicalBook CAS DataBase List 13-Oxa-2,6,11-triazapentadecanoic acid, 14,14-dimethyl-12-oxo-,1,1-dimethylethyl ester
83392-10-3

13-Oxa-2,6,11-triazapentadecanoic acid, 14,14-dimethyl-12-oxo-,1,1-dimethylethyl ester synthesis

13synthesis methods
-

Yield:83392-10-3 100%

Reaction Conditions:

in tetrahydrofuran at 0; for 1 h;

Steps:

4

To a solution of spermidine (3.0 g, 20.6 mmol) in THF ( 100 mL) was slowly added a solution of 2-(Boc-oxyimino)-2-phenylacetonitrile (10.14 g, 20.6 mmol) in THF (20 mL) at 0 0C. The reaction mixture was stirred at 0 °C for 1 hour and then the solvent was evaporated under vacuum. The residue was filtrated on silica gel and eluted with CH2CI2: EtOAc 7:3 and then with CH2Cl2:MeOH 1 : 1 to afford tert-butyl 4-(3-(tert-butyl carbamate) propyl) butylcarbamate 16 (5.3 g, > 100%) as a colourless oil. 1H NMR (300 MHz, CD3OD) δ 3.15 (t, J= 6.8 Hz, 2H), 3.08 (t, J= 6.8 Hz, 2H), 3.00 (t, J= 6.8 Hz, 4H), 1.83 (m, 2H), 1.69 (m, 2H), 1.55 (m, 2H), 1.44 (bs, 18H). MS (APCI): 346 (M+ l)+. Rf= 0.18 (CH2Cl2:MeOH, 8:2).

References:

WO2006/117197,2006,A1 Location in patent:Page/Page column 14; 23