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ChemicalBook CAS DataBase List Ethyl N-(2-butyl)glycinate

Ethyl N-(2-butyl)glycinate synthesis

2synthesis methods
33966-50-6 Synthesis
SEC-BUTYLAMINE

33966-50-6
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105-36-2 Synthesis
Ethyl bromoacetate

105-36-2
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Yield:82560-46-1 91%

Reaction Conditions:

in tetrahydrofuran;diethyl ether;

Steps:

1 Preparation of sec-butylamino-acetic Acid Ethyl Ester

Example 1 Preparation of sec-butylamino-acetic Acid Ethyl Ester Synthesis was carried out in analogous manner to the literature procedure: J. A Kruijtzer, L. J. F. Hofmeyer, W. Heerma, C. Versluis, R. M. J. Liskamp, Chem. Eur. J., 4(8), pp. 1570-1580 (1998). Ethyl bromoacetate (50 mmol) in tetrahydrofuran (25 mL, THF) was added dropwise to a cooled solution of sec-butylamine (110 mmol) in THF (25 mL) over 5 min. After stirring for 4 h at room temperature, the reaction mixture was concentrated in vacuo and resuspended in dry diethyl ether. The mixture was filtered to remove sec-butylamine hydrobromide, the residue washed with ether, and the filtrate concentrated in vacuo. Yield 91% as a colourless oil. 1H NMR (250 MHz, 298° K, CDCl3, ppm) δ0.87 (t, 3H, J=7.5 Hz), 1.00 (d, 3H, J=6.3 Hz), 1.25 (t, 3H, J=7.2 Hz), 1.43 (m, 2H), 1.83 (br, 1H), 2.52 (m, 1H), 3.38 (s, 2H), 4.16 (q, 2H, J=7.2 Hz); 13C NMR (62.90 MHz, 298° K, CDCl3) 10.24, 14.32, 19.66, 29.58, 54.32, 60.81, 172.86.

References:

US2002/146684,2002,A1

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