L-Threonine, methyl ester, hydrochloride (1:1)
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L-Threonine, methyl ester, hydrochloride (1:1)
structure -
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CAS No:
39994-75-7
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Formula:
C5H11NO3.ClH
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Chemical Name:
L-Threonine, methyl ester, hydrochloride (1:1)
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Synonyms:
L-Threonine,methyl ester,hydrochloride (1:1);L-Threonine,methyl ester,hydrochloride;Threonine,methyl ester,hydrochloride,L-;Methyl L-threoninate hydrochloride;Methyl (2S,3R)-2-amino-3-hydroxybutanoate hydrochloride;(2S,3R)-2-Amino-3-hydroxybutanoic acid methyl ester hydrochloride;1384246-03-0
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CAS No:
L-Threonine, methyl ester, hydrochloride (1:1) Basic Attributes
169.61
169.050568
254-738-5
DTXSID20193049
29225000
Characteristics
72.6
0.36980
White Powder
122-124 °C
274.4ºC at 760 mmHg
119.8ºC
soluble in water.
−20°C
L-Threonine, methyl ester, hydrochloride (1:1) Use and Manufacturing
L-Threonine was dissolved in methanalic HCl solution (2M)and refluxed the reaction mixture for 1 h. Then the organicsolvent was evaporated using rotary evaporator and againsame methanalic HCl solution was added to the reactionmixture and refluxed for 1 h. After the reaction time, theorganic solvent was evaporated under reduced pressure togive white solid compound. ESI–MS: m/z at 134.2 [M+ +H].A 250 ml 3-necked round-bottom flask was equipped with a condenser, a dropping funnel and a rubber septum. The condenser was fitted with a calcium chloride drying tube. The dropping funnel was charged with acetyl chloride (23.0 ml, 0.33 mol). The flask was filled with 75 mls of methanol and cooled to 0 °C in an ice bath under nitrogen. The acetyl chloride is added dropwise over 5 min before L-threonine (13.58 g, 0.11 mol) was added before heating to reflux temperature. After 2 h the solvent is removed in vacuo to yield a white fluffy solid (18.75 g, 97percent), which was used without further purification. A mixture of 10 (5.4 g, 24.6 mmol) and 6 N HCl (60 mL) was refluxed for 5 h, and after cooling to ambient temperature, the reaction mixture was extracted with diethyl ether (3×70 mL) to remove benzoic acid. The aqueous layer was evaporated to dryness under reduced pressure, and the residue was further dried under high vacuum overnight to afford crude allo-L-threonine. MeOH (25 mL) was cooled to 0 C, and thionyl chloride (1.80 mL, 25.2 mmol) was added dropwise. To the resulting HCl methanol solution was added the crude allo-L-threonine, and the reaction mixture was heated under reflux for 1 h. The solvent was removed in vacuo, and another batch of HCl methanol solution (prepared in the same manner) was added, and then the reaction mixture was heated under reflux for another 1 h. The solvent was removed in vacuo to obtain General procedure: SOCl2 (1.5 eq) was added dropwise to stirring anhydrous MeOH (2 M) at 0 C, followed by L-amino acid (1 eq) portion-wise. The mixture was heated to 40 C and stirred at this temperature for 3 h. The solvent was then evaporated under reduced pressure to give methyl ester hydrochlorides 1a-d.General procedure: The ester hydrochloride of the L-amino acid 1a-c (1.0 eq) was suspended in petroleum ether. Triethylamine (1.5 eq) and trimethylacetaldehyde (1.2 eq) were then added. The mixture was heated at reflux with continuous removal of water using a Dean- Stark apparatus for 18 h. The white precipitate was then filtered and washed with Et2O. The combined filtrates were concentrated under reduced pressure to furnish the oxazolidines or thiazolidine.
Computed Properties
Molecular Weight:169.61
Hydrogen Bond Donor Count:3
Hydrogen Bond Acceptor Count:4
Rotatable Bond Count:3
Exact Mass:169.0505709
Monoisotopic Mass:169.0505709
Topological Polar Surface Area:72.6
Heavy Atom Count:10
Complexity:104
Defined Atom Stereocenter Count:2
Covalently-Bonded Unit Count:2
Compound Is Canonicalized:Yes
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