L-P-HYDROXYPHENYLGLYCINE METHYL EST

L-P-HYDROXYPHENYLGLYCINE METHYL EST Property

Melting point:

179-183 °C(lit.)

storage temp. 

Inert atmosphere,Room Temperature

solubility 

Aqueous Acid (Slightly), DMSO (Slightly), Methanol (Slightly)

form 

Solid

color 

White

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H302Harmful if swallowed

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P301+P312IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.

P302+P352IF ON SKIN: wash with plenty of soap and water.

P304+P340IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

L-P-HYDROXYPHENYLGLYCINE METHYL EST Chemical Properties,Usage,Production

Uses

Methyl (2S)-2-amino-2-(4-hydroxyphenyl)acetate Hydrochloride acts as a reagent in the synthesis of Amoxicillin, an antibiotic for the treatment of bacterial infection.

Synthesis

General procedure for the synthesis of D-p-hydroxyphenylglycine methyl ester hydrochloride from methanol and (R)-2-amino-2-(4-hydroxyphenyl)acetic acid: under nitrogen protection and -15 °C, thionyl chloride (1.5 mL, 33.0 mmol) was slowly added dropwise to anhydrous methanol (25 mL) in (R)-4-hydroxyphenylglycine (5.00 g, 29.91 mmol) ) suspension while stirring. The reaction mixture was gradually warmed to room temperature and stirred continuously overnight. Subsequently, the yellow solution was refluxed for 30 min. The reaction mixture was concentrated under reduced pressure to give D-p-hydroxyphenylglycine methyl ester hydrochloride in the form of an off-white solid. The hydrochloride was stirred in ether (15 mL), filtered, washed with ether (2 x 15 mL) and dried to give the final D-p-hydroxyphenylglycine methyl ester hydrochloride (6.50 g, 100%) as a white solid with a melting point of 189-191 °C; specific optical rotation [α]20D = -120.9 (c 1, 1M HCl), literature value [α]25D = - 121.1 (c 1, 1M HCl); IR spectra (KBr) νmax/cm-1: 3339 (broad peak), 1740 (C=O), 1595; NMR hydrogen spectrum (300 MHz, DMSO-d6) δH: 3.68 (3H, single peak, OCH3), 5.11 (1H, single peak, C(2)H), 6.80 (2H, double peak. J=8.5 Hz, aromatic H), 7.25 (2H, double peak, J=8.5 Hz, aromatic H), 8.70 (3H, broad peak, NH3), 9.86 (1H, single peak, OH).

References

[1] Tetrahedron Asymmetry, 2013, vol. 24, # 20, p. 1265 - 1275
[2] European Journal of Medicinal Chemistry, 2018, vol. 145, p. 649 - 660
[3] Synthesis, 2012, vol. 44, # 6, p. 875 - 880
[4] Croatica Chemica Acta, 2003, vol. 76, # 1, p. 23 - 36
[5] Heterocycles, 2009, vol. 78, # 6, p. 1477 - 1483