L-Glutamic acid dimethyl ester hydrochloride synthesis
- 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
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
782 suppliers
$7.29/5ml-f
56-86-0
864 suppliers
$5.00/25g
23150-65-4
333 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
67-56-1
782 suppliers
$7.29/5ml-f
1499-55-4
300 suppliers
$6.00/5g
23150-65-4
333 suppliers
$6.00/10g
67-56-1
782 suppliers
$7.29/5ml-f
56-86-0
864 suppliers
$5.00/25g
77-76-9
395 suppliers
$9.00/5ml
23150-65-4
333 suppliers
$6.00/10g
