Glycine methyl ester hydrochloride

Glycine methyl ester hydrochloride
Names
IUPAC name
Methyl glycinate hydrochloride
Systematic IUPAC name
Methyl 2-aminoacetate hydrochloride
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.024.672 Edit this at Wikidata
EC Number
  • 227-139-1
UNII
  • InChI=1S/C3H7NO2.ClH/c1-6-3(5)2-4;/h2,4H2,1H3;1H
    Key: COQRGFWWJBEXRC-UHFFFAOYSA-N
  • COC(=O)CN.Cl
Properties
C3H8ClNO2
Molar mass 125.55 g·mol−1
Appearance white solid
Melting point 175–176 °C (347–349 °F; 448–449 K)
Hazards
GHS labelling:[1]
GHS07: Exclamation mark
Warning
H315, H319, H335
P261, P264, P271, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P403+P233, P405, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Glycine methyl ester hydrochloride is the organic compound with the formula [CH3O2CCH2NH3]Cl. A white, water-soluble solid, it is the hydrochloride of the methyl ester of the amino acid glycine.

Synthesis and reactions

Glycine methyl ester hydrochloride can be prepared by treatment of glycine with 2 equivalents of trimethylsilyl chloride, followed by the addition of methanol.[2][3]

Upon treatment with base, the salt converts to glycine methyl ester.[4]

Glycine methyl ester (and other esters of glycine) are not shelf-stable, tending to polymerize when stored at room temperature[4] or convert to diketopiperazine. The hydrochloride is shelf-stable.

References

  1. ^ "Glycine methyl ester hydrochloride". pubchem.ncbi.nlm.nih.gov. Retrieved 24 January 2022.
  2. ^ Li, Jiabo; Sha, Yaowu (2008). "A Convenient Synthesis of Amino Acid Methyl Esters". Molecules. 13 (5): 1111–1119. doi:10.3390/molecules13051111. PMC 6245331. PMID 18560331.
  3. ^ White, James D.; Kranemann, Christian L.; Kuntiyong, Punlop (2002). "4-Methoxycarbonyl-2-methyl-1,3-oxazole". Org. Synth. 79: 244. doi:10.15227/orgsyn.079.0244.
  4. ^ a b Myers, Andrew G.; Gleason, James L. (1999). "Asymmetric Synthesis of α-Amino Acids by the Alkylation of Pseudoephedrine Glycinamide: L-Allylglycine and N-BOC-l-Allylglycine". Organic Syntheses. 76: 57. doi:10.15227/orgsyn.076.0057.