L-Glutamic acid 1-ethyl ester synthesis
- Product Name:L-Glutamic acid 1-ethyl ester
- CAS Number:52454-78-1
- Molecular formula:C7H13NO4
- Molecular Weight:175.18
5672-81-1
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52454-78-1
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Yield: 93%
Reaction Conditions:
with palladium 10% on activated carbon;hydrogen in ethanol for 2.5 h;
Steps:
3.5.3. L-Glutamic Acid α-ethyl Ester (11)
The solution of 17 (5.0 g, 16.2 mmol) in EtOH (150 mL) was hydrogenated in the presence 10% Pd/C (0.4 g) for 2.5 h. After filtration through a Celite pad, the solution was evaporated and dropped into Et2O (50 mL). After cooling in the refrigerator, the white precipitate was filtered, washed with Et2O, and dried in vacuum at 30 °C to give 11 (2.6 g, 93%). TLC: RF = 0.65 (CHCl3/MeOH/NH3 2:2:1); [α]20D = +27.0 (c = 2, 1 M HCl); Mp. 90 °C; 1H-NMR δ: 5.00 (3H, very broad s, -NH2 and -COOH), 4.10 (2H, m, -CH2CH3), 3.37 (1H, m,-CHNH2), 2.29 (2H, m, both H of CH2β), 1.83 and 1.64 (2H, 2m, both H of CH2α), 1.20 (3H, t, J = 7.0 Hz, -CH2CH3); 13C-NMR δ: 174.80 (COα), 174.26 (COγ), 60.20 (-CH2CH3), 53.12 (-CHNH2), 30.84 (CH2β), 29.18(CH2α), 14.07 (-CH2CH3); 15N-NMR δ: -351.5; HRMS: calcd for C7H14NO4 m/z = 176.0923, found m/z = 176.0926.
References:
Michalak, Olga;Gruza, Mariusz M.;Witkowska, Anna;Bujak, Iwona;Cmoch, Piotr [Molecules,2015,vol. 20,# 6,p. 10004 - 10031]
64-17-5
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1119-33-1
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52454-78-1
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