Alanine methyl ester hydrochloride
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Alanine methyl ester hydrochloride
structure -
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CAS No:
2491-20-5
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Formula:
C4H9NO2.ClH
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Chemical Name:
Alanine methyl ester hydrochloride
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Synonyms:
L-Alanine,methyl ester,hydrochloride (1:1);Alanine,methyl ester,hydrochloride,L-;L-Alanine,methyl ester,hydrochloride;Alanine methyl ester hydrochloride;Methyl L-alaninate hydrochloride;(S)-Alanine methyl ester hydrochloride;Methyl alaninate hydrochloride;L-Alanine methyl ester hydrochloride salt;(S)-2-Aminopropionic acid methyl ester hydrochloride;NSC 29729;Methyl (S)-2-aminopropanoate hydrochloride;(L)-Ala-OMe hydrochloride;L-Alanine methyl ester hydrogen chloride;Methyl (2S)-2-aminopropanoate hydrochloric acid
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CAS No:
Characteristics
52.3
1.00890
White to off-white Powder
108 °C
101.5ºC at 760 mmHg
6.5 ° (C=2, MeOH)
soluble in water (100 mg/ml).
−20°C
35mmHg at 25°C
7 º (c=2, CH3OH 24 ºC)
Safety Information
NONH for all modes of transport
3
36/37/38
24/25-36-26
Xi
P261, P264, P271, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P403+P233, P405, P501
H315
|Warning|H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]|P261, P264, P271, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P403+P233, P405, and P501|Aggregated GHS information provided by 4 companies from 3 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Alanine methyl ester hydrochloride Use and Manufacturing
The L-alanine was used as substrate to produce (S)-alanine methyl ester hydrochloride (1a) according to the literature. (Xing et al., 2012). Add 15 mL of absolute methanol to the round bottom flask. Slow-drop 2.16 mL of SOClSOClTake 125mL of methanol and add it to a 250mL three-necked flask (ensure that the environment is anhydrous during the reaction, with a drying device; the reaction will generate HCl and SO2 gas, use a lye absorption device) and cool it in a constant temperature reaction bath to - At 14°C, 10 mL (0.138 mol) of SOCl2 was slowly added dropwise with magnetic stirring. The reaction temperature was controlled to be below -10°C during the dropwise addition, and the reaction was continued for 1 h after the addition was completed. The reaction solution was transferred to a 250 mL round-bottomed flask, and the temperature was naturally raised to room temperature. 12.21 g (0.137 mol) of alanine was added and the reaction was stopped by heating to reflux under magnetic stirring for 4 hours. The product was evaporated and the solvent was distilled off to give alanine methyl ester hydrochloride as a yellow viscous liquid with a yield of 98percent. It can be used directly in the next step without purification.General procedure: A suspension of L-amino acid (50mmol) in methanol (50mL) was stirred under ice cold conditions. Thionyl chloride (5mL) was slowly dropped to the solution at−5°C. Then, the mixture was allowed to slowly warm to room temperature while being stirred. The reaction was monitored by TLC (N-butanol: water: acetic acid=4:1:1). When the reaction was completed, the solvent was evaporated under reduced pressure to afford the crude product, which was recrystallized from methanol/ether to give a white solid.To a solution of L-alanine (5.0 g, 56 mmol) in methanol (60 mL) at -20°C was added dropwise thionyl chloride (6.1 mL, 84 mmol) and the mixture was stirred at ambient temperature overnight. The solvent was removed in vacuo. The solid residue was washed with diethyl ether, filtered and dried under vacuum to afford the title compound as a white solid (7.7 g). The crude product was used without further purification in subsequent reactions.1 H NMR (500 MHz, d4-MeOH) δ 4.1 1 (q, 1 H), 3.84 (s, 3H), 1.54 (d, 3H).Add L-alanine (2.5 g, 27.8 mmol) to a dry flask.Add anhydrous anaerobic methanol (278 mL), stir at 0 ° C for 10 min, Thionyl chloride (0.5 mL) was slowly added thereto, and the reaction was stirred for 6 hours.After the reaction was completed, the solvent was evaporated, diluted with diethyl ether and filtered.L-Alanine methyl ester 13 was obtained as a white solid, 3.36 g.General procedure: For the synthesis of compounds 2a, 2c–2g, we used slightly modificated known procedure [1]. To a stirred solution of amino acid (32.2mmol) in dry methanol (100mL) was added drop-wise thionyl chloride (64.4mmol). The temperature was kept between−10 and−5°C. After complete addition, the reaction was stirred at RT overnight. After 16h, the solution was evaporated to dryness. The product was diluted with EtOAc and collected by filtration. The residue was dried under reduced pressure to give an amino acid methyl ester hydrochloride as white crystalline powder. The yields were higher in all experiments than 80percent. Melting point and
Used in biochemical reagents and pharmaceutical intermediates.
Computed Properties
Molecular Weight:139.58
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:2
Exact Mass:139.0400063
Monoisotopic Mass:139.0400063
Topological Polar Surface Area:52.3
Heavy Atom Count:8
Complexity:72.1
Defined Atom Stereocenter Count:1
Covalently-Bonded Unit Count:2
Compound Is Canonicalized:Yes
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Alanine methyl ester hydrochloride
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