ChemicalBook CAS DataBase List Carbamic acid, [2-(2-aminoethoxy)ethyl]-, 1,1-dimethylethyl ester (9CI)

Carbamic acid, [2-(2-aminoethoxy)ethyl]-, 1,1-dimethylethyl ester (9CI) synthesis

6synthesis methods

Product Name:Carbamic acid, [2-(2-aminoethoxy)ethyl]-, 1,1-dimethylethyl ester (9CI)
CAS Number:127828-22-2
Molecular formula:C9H20N2O3
Molecular Weight:204.27

2752-17-2 Synthesis

2752-17-2
162 suppliers
$65.00/1 G

24424-99-5 Synthesis

24424-99-5
822 suppliers
$13.50/25G

Carbamic acid, [2-(2-aminoethoxy)ethyl]-, 1,1-dimethylethyl ester (9CI)

127828-22-2
140 suppliers
$25.00/250mg

Yield:127828-22-2 71.5%

Reaction Conditions:

in tetrahydrofuran at 0 - 20;

Steps:

4.2. N-(tert-Butyloxycarbonyl)-2,2'-oxybis(ethylamine) (1)
This compound was synthesized according to the procedure described previously with slight modifications.²⁵ To a cooled (0 °C) solution of 2,2'-oxybis(ethylamine) (10.0 mL, 94.1 mmol) in methanol (1000 mL) was added dropwise a solution of di-tert-butyl dicarbonate ((Boc)₂O; 10.3 g, 47.0 mmol) in THF (300 mL), and the mixture was stirred for 1 h at the same temperature and additional 24 h at room temperature. After removing the solvent in vacuo, the residue was dissolved in 1 N NaOH (200 mL), and extracted with chloroform (300 mL × 3). The organic phases were combined, dried over anhydrous MgSO₄. The solvent was removed in vacuo to provide 1 as a colorless oil (6.88 g, 71.5%). ¹H NMR (CDCl₃): δ 1.39 (9H, s, Boc), 2.79-2.82 (2H, t, CH₂), 3.24-3.28 (2H, dd, CH₂), 3.41-3.43 (2H, t, CH₂), 3.44-3.47 (2H, t, CH₂), 5.00 (1H, d, NH). ESI-MS (M+H)⁺: m/z 205, found: 205

References:

Suzuki, Hiroyuki;Kanai, Ayaka;Uehara, Tomoya;Guerra Gomez, Francisco L.;Hanaoka, Hirofumi;Arano, Yasushi [Bioorganic and Medicinal Chemistry,2012,vol. 20,# 2,p. 978 - 984] Location in patent:experimental part

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