Glycine methyl ester hydrochloride explained

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.^{[1] [2]}

Upon treatment with base, the salt converts to glycine methyl ester.^[3]

Glycine methyl ester (and other esters of glycine) are not shelf-stable, tending to polymerize when stored at room temperature^[3] or convert to diketopiperazine. The hydrochloride is shelf-stable.

Notes and References

1. 10.3390/molecules13051111 . free . A Convenient Synthesis of Amino Acid Methyl Esters . 2008 . Li . Jiabo . Sha . Yaowu . Molecules . 13 . 5 . 1111–1119 . 18560331 . 6245331.
2. 10.15227/orgsyn.079.0244 . James D. . White . Christian L. . Kranemann . Punlop . Kuntiyong . Org. Synth. . 2002 . 79 . 244 . 4-Methoxycarbonyl-2-methyl-1,3-oxazole.
3. Asymmetric Synthesis of α-Amino Acids by the Alkylation of Pseudoephedrine Glycinamide: L-Allylglycine and N-BOC-l-Allylglycine . Myers . Andrew G. . Gleason . James L. . Organic Syntheses . 1999 . 76 . 57 . 10.15227/orgsyn.076.0057.