ChemicalBook CAS DataBase List L-Glutamic acid dimethyl ester hydrochloride

L-Glutamic acid dimethyl ester hydrochloride synthesis

8synthesis methods

Product Name:L-Glutamic acid dimethyl ester hydrochloride
CAS Number:23150-65-4
Molecular formula:C7H14ClNO4
Molecular Weight:211.64

67-56-1

56-86-0

L-Glutamic acid dimethyl ester hydrochloride

23150-65-4

To a 500 mL four-necked flask equipped with a stirrer, thermometer and reflux condenser (connected to a 30% aqueous sodium hydroxide solution absorption unit), 300 g of methanol, 14.7 g (0.10 mol) of L-glutamic acid, and 30.0 g (0.25 mol) of thionyl chloride were added sequentially. The reaction mixture was heated to 60-63 °C and the reaction was stirred at this temperature for 7 hours. Upon completion of the reaction, the system was cooled to 20-25 °C, followed by the passage of nitrogen to displace the hydrogen chloride gas in the system for 30 min. Next, the excess thionyl chloride and methanol were recovered by distillation. To the residue, 100 g of methyl tert-butyl ether was added and pulped, followed by filtration to collect the solid. Upon drying, 20.8 g of L-glutamic acid dimethyl ester hydrochloride was obtained as a white solid. The product was analyzed by high performance liquid chromatography (HPLC) with 99.5% purity and 98.1% yield.

67-56-1 Synthesis

67-56-1
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56-86-0 Synthesis

56-86-0
919 suppliers
$5.00/25g

23150-65-4
338 suppliers
$6.00/10g

Yield:23150-65-4 100%

Reaction Conditions:

Stage #1:methanol with thionyl chloride at 0; for 0.5 h;
Stage #2:L-glutamic acid at 21; for 72 h;Inert atmosphere;

Steps:

6 PREPARATION EXAMPLE 6 Dimethyl L-glutamate hydrochloride ( 6-HCI )
Thionyl chloride (5.0 mL, 68 mmol) was added dropwise to 50 mL of anhydrous MeOH at 0 °C. The mixture was stirred for 30 min at the same temperature followed by addition of L-glutamic acid 17 (5.0 g, 34 mmol) . The reaction was stirred under a N₂ atmosphere for 3 days at 21 °C and concentrated in vacuo to afford 6-HCI (7.19 g, quant.) as a colorless solid. The crude product was used without further purification. ^XH NMR (400 MHz, D₂0) δ 4.24 - 4.19 (m, 1H), 3.85 (s, 3H), 3.73 (s, 3H), 2.65 (td, J = 7.3, 2.2 Hz, 2H), 2.37 - 2.13 (m, 2H) ; ¹³C NMR (101 MHz, D₂0) δ 174.8, 170.2, 53.6, 52.4, 52.0, 29.2, 24.7.

References:

DANMARKS TEKNISKE UNIVERSITET;PEIRó CADAHíA, Jorge;CLAUSEN, Mads, Hartvig;BONDEBJERG, Jon;HANSEN, Christian, Abildgaard WO2018/37120, 2018, A1 Location in patent:Page/Page column 27; 32

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67-56-1 Synthesis

67-56-1
803 suppliers
$7.29/5ml-f