Glycine, N-(phenylMethyl)-, Methyl ester

Glycine, N-(phenylMethyl)-, Methyl ester Property

Boiling point:

130-132 °C(Press: 6 Torr)

Density 

1.069±0.06 g/cm3(Predicted)

storage temp. 

under inert gas (nitrogen or Argon) at 2–8 °C

pka

6.46±0.20(Predicted)

Appearance

Colorless to light yellow Liquid

Safety

RIDADR 

3265

HazardClass 

8

PackingGroup 

Ⅲ

Hazard and Precautionary Statements (GHS)

Glycine, N-(phenylMethyl)-, Methyl ester Chemical Properties,Usage,Production

Synthesis

The general procedure for the synthesis of methyl 2-(benzylamino)acetate from methyl bromoacetate and benzylamine was as follows: the flame-dried flask was cooled under nitrogen protection and a tetrahydrofuran (THF, 10 mL, 1 M) solution of benzylamine (2.36 mL, 21.6 mmol) was added. The reaction system was cooled to 0 °C, followed by slow dropwise addition of methyl bromoacetate (0.93 mL, 9.8 mmol). The reaction mixture was controlled to gradually warm up to room temperature over 2.5 h and the progress of the reaction was monitored by thin layer chromatography (TLC) until the feedstock was completely consumed. After completion of the reaction, the mixture was concentrated under reduced pressure and the resulting residue was dissolved in ether (Et2O) and filtered. The filtrate was concentrated again under reduced pressure and the crude product was purified by fast column chromatography to give 1.12 g (63% yield) of methyl 2-(benzylamino)acetate as a colorless oil. Its nuclear magnetic resonance hydrogen spectrum (1H NMR, 500 MHz, CDCl3) data were as follows: δ 7.30 (d, J = 4.3 Hz, 4H), 7.29-7.24 (m, 1H), 3.81 (s, 2H), 3.73 (s, 3H), 3.43 (s, 2H), 1.93 (s, br, 1H), which is in accordance with the literature reports.

References

[1] Journal of Labelled Compounds and Radiopharmaceuticals, 2001, vol. 44, # 12, p. 831 - 841
[2] Patent: US2002/151546, 2002, A1
[3] Bulletin de la Societe Chimique de France, 1993, vol. 130, p. 584 - 596
[4] Journal of Organic Chemistry, 1998, vol. 63, # 8, p. 2442 - 2450
[5] Tetrahedron Letters, 2015, vol. 56, # 23, p. 3393 - 3395