Glycine_methyl_ester_hydrochloride Knowpia

Glycine methyl ester hydrochloride
Names
	IUPAC name Methyl glycinate hydrochloride
	Systematic IUPAC name Methyl 2-aminoacetate hydrochloride
Identifiers
CAS Number	5680-79-5 ;
3D model (JSmol)	Interactive image;
ECHA InfoCard	100.024.672
EC Number	227-139-1;
PubChem CID	122755;
CompTox Dashboard (EPA)	DTXSID20205358 ;
	InChI InChI=1S/C3H7NO2.ClH/c1-6-3(5)2-4;/h2,4H2,1H3;1H Key: COQRGFWWJBEXRC-UHFFFAOYSA-N;
	SMILES COC(=O)CN.Cl;
Properties
Chemical formula	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:
Pictograms
Signal word	Warning
Hazard statements	H315, H319, H335
Precautionary statements	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). Infobox references

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 edit

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 edit

^ "Glycine methyl ester hydrochloride". pubchem.ncbi.nlm.nih.gov. Retrieved 24 January 2022.
^ 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.
^ 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.
^ ^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.

[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.

[myers1-4] 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.

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Summary

Synthesis and reactions edit

References edit