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Glycine methyl ester hydrochloride

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Glycine methyl ester hydrochloride Basic information
Product Name:Glycine methyl ester hydrochloride
Synonyms:AMINOACETIC ACID METHYL ESTER HYDROCHLORIDE;METHYL GLYCINATE HCL;METHYL GLYCINATE HYDROCHLORIDE;L-GLYCINE METHYL ESTER HYDROCHLORIDE;GLYCINE-OME HCL;GLYCINE METHYL ESTER HCL;GLYCINE METHYL ESTER HYDROCHLORIDE;GLYCINE METHYL ESTER HYDROCHLORIDE SALT
CAS:5680-79-5
MF:C3H8ClNO2
MW:125.55
EINECS:227-139-1
Product Categories:Pharmaceutical intermediates;Amino Acids & Derivatives;Amino hydrochloride;Amino Acid Derivatives;Glycine;Peptide Synthesis;Glycine [Gly, G];Amino Acids and Derivatives;Amino Acids;straight chain compounds;bc0001
Mol File:5680-79-5.mol
Glycine methyl ester hydrochloride Structure
Glycine methyl ester hydrochloride Chemical Properties
Melting point 175 °C (dec.)(lit.)
density 1.000
storage temp. Inert atmosphere,Room Temperature
solubility >1000 g/L (20°C)
form Powder or Cyrstals
color White
Water Solubility >1000 g/L (20 ºC)
Sensitive Hygroscopic
BRN 3593644
Stability:Stable. Incompatible with strong oxidizing agents.
Major Applicationpeptide synthesis
InChIInChI=1S/C3H7NO2.ClH/c1-6-3(5)2-4;/h2,4H2,1H3;1H
InChIKeyCOQRGFWWJBEXRC-UHFFFAOYSA-N
SMILESC(=O)(OC)CN.Cl
CAS DataBase Reference5680-79-5(CAS DataBase Reference)
Safety Information
Safety Statements 22-24/25
WGK Germany 3
HS Code 29224995
Storage Class11 - Combustible Solids
MSDS Information
ProviderLanguage
Methyl glycinate hydrochloride English
ACROS English
SigmaAldrich English
ALFA English
Glycine methyl ester hydrochloride Usage And Synthesis
Chemical PropertiesCrystalline
UsesA Glycine ester, a non-essential amino acid for human development.
UsesGlycine methyl ester hydrochloride a non-essential amino acid used for human development.
reaction suitabilityreaction type: solution phase peptide synthesis
Synthesis
Methanol

67-56-1

Glycine

56-40-6

Glycine methyl ester hydrochloride

5680-79-5

(2) Preparation of glycine methyl ester hydrochloride: 60 mL of methanol was added to a 100 mL round-bottomed flask under ice-bath conditions, followed by the slow dropwise addition of 4 mL of sulfoxide chloride (SOCl2) through a constant-pressure dropping funnel (with a drying tube on top). The resulting off-gas was absorbed using NaOH solution. After stirring the reaction mixture for 1 h, 8 mmol of glycine was added and stirring was continued for 30 min at room temperature. Subsequently, the reaction system was warmed up to 66 °C and refluxed for 6 hours. The progress of the reaction was monitored by thin layer chromatography (TLC) using 2% ninhydrin ethanol solution as a color developer until the disappearance of the raw material spot. After completion of the reaction, the solvent was removed by evaporation to give glycine methyl ester hydrochloride in 100% yield.

Purification MethodsCrystallise the ester salt from MeOH. [Werbin & Spoerri J Am Chem Soc 69 1682 1947, Beilstein 4 H 340, 4 III 1116.]
References[1] Synthetic Communications, 1998, vol. 28, # 3, p. 471 - 474
[2] European Journal of Organic Chemistry, 2012, # 29, p. 5774 - 5788,15
[3] European Journal of Organic Chemistry, 2012, # 29, p. 5774 - 5788
[4] Patent: US2014/206741, 2014, A1. Location in patent: Paragraph 0131
[5] European Journal of Organic Chemistry, 2017, vol. 2017, # 3, p. 695 - 703
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