Methanol → Methyl 2-(2-Aminoacetamido)Acetate

Reaktionsgleichung

[NH2:1][CH2:2][C:3]([NH:5][CH2:6][C:7]([OH:9])=[O:8])=[O:4].S(Cl)(Cl)=O.[CH3:14]O>>[NH2:1][CH2:2][C:3]([NH:5][CH2:6][C:7]([O:9][CH3:14])=[O:8])=[O:4]

Komponenten

Edukt 3

HCID 887Methanol

HCID 11163Glycylglycine

HCID 24386Thionyl Chloride

Produkt 1

HCID 3248350Methyl 2-(2-Aminoacetamido)Acetate

Versuchsvorschrift

2.5 g (19 mmoles) of Gly-Gly-OH was suspended in 25 mL of dry methanol. Two equivalents of thionyl chloride were added, and the suspension stirred to dissolution. The mixture was allowed to sit at room temperature overnight. The solvent was removed under vacuum, the residue taken up in a minimum of methanol, and anhydrous ether added to effect crystallization. Yield 3.2 g (92%). M.P. 146°-146° C. 1H-NMR (DMSO) 3.6 (s, 3H OMe), 3.8 and 3.9 (d, 2H, Gly α-H's).