Methanol → Methyl 2-(2-Aminoacetamido)Acetate

HRID 1196812Notes

Reaction equation

HRID 1196812 reaction equation
[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]

Participants

4

Reactant 3

HCID 887MethanolHCID 11163GlycylglycineHCID 24386Thionyl Chloride

Product 1

HCID 3248350Methyl 2-(2-Aminoacetamido)Acetate

Procedure

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).

Workup

  1. customThe solvent was removed under vacuum
  2. additionadded to effect crystallization

Sources & evidence

ORD record
ord-fc8851893076401a9a5849d488c88b6c
Source dataset
uspto-grants-1992_05
Patent number
US05116741

Reaction notes

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