Methyl D-(-)-4-hydroxy-phenylglycinate Chemical Properties

Melting point:

169-172°C

Boiling point:

303.2±27.0 °C(Predicted)

Density 

1.248±0.06 g/cm3(Predicted)

vapor pressure 

0.083Pa at 25℃

storage temp. 

Room Temperature

solubility 

DMSO (Slightly), Ethanol (Slightly, Sonicated), Methanol (Slightly)

form 

Solid

pka

9.74±0.26(Predicted)

color 

White to Off-White

InChI

InChI=1S/C9H11NO3/c1-13-9(12)8(10)6-2-4-7(11)5-3-6/h2-5,8,11H,10H2,1H3

InChIKey

SZBDOFWNZVHVGR-UHFFFAOYSA-N

SMILES

C(OC)(=O)C(N)C1=CC=C(O)C=C1

Methyl D-(-)-4-hydroxy-phenylglycinate Usage And Synthesis

Uses

Methyl D-(-)-4-Hydroxy-phenylglycinate is useful for the synthesis (+)-radicamine B. Also, it is used for the preparation of amoxicillin.

Flammability and Explosibility

Non flammable

Synthesis

Step 1: (R)-2-Amino-2-(4-hydroxyphenyl)acetic acid (D-4-hydroxyphenylglycine, 10.0 g, 60.1 mmol) was dissolved in methanol (200 mL), thionyl chloride (8 mL) was added slowly dropwise, and the reaction was stirred for 10 hours at room temperature. After completion of the reaction, the mixture was concentrated under reduced pressure and the residue was washed twice with ether to afford methyl (R)-2-amino-2-(4-hydroxyphenyl)acetate (D-4-hydroxyphenylglycine methyl ester, 13.0 g, 60.0 mmol, 100% yield) as a white solid.1H NMR (300 MHz, DMSO-d6) δ 3.68 (s, 3H), 5.07 (s, 1H), 6.85 (d, J = 8.5 Hz, 2H), 7.29 (d, J = 8.6 Hz, 2H), 9.03 (s, 3H), 10.02 (s, 1H). Step 2: Methyl (R)-2-amino-2-(4-hydroxyphenyl)acetate (D-4-hydroxyphenylglycine methyl ester, 0.302 g, 1.39 mmol) was dissolved in freshly prepared glyoxylate (1.27 g, 13.8 mmol) and copper(II) sulfate pentahydrate (0.35 g, 1.40 mmol) in a 2.5 M pyridine buffer and a 0.5 M acetic acid in aqueous solution and stirred for 10 h at room temperature. The reaction solution was extracted with dichloromethane (3 × 10 mL), the organic layers were combined, washed with 0.5 M HCl (3 × 20 mL), dried, filtered and concentrated under reduced pressure. The residue was purified by fast column chromatography (silica gel, chloroform elution) to afford methyl 2-(4-hydroxyphenyl)-2-oxoacetate (0.109 g, 6.06 mmol, 44% yield) as a clear oil.1H NMR (300 MHz, CDCl3) δ 3.99 (s, 3H), 5.41 (br s, 1H), 6.95 (d, J = 8.8 Hz, 2H), 8.00 (d, J = 8.8 Hz, 2H).

References

[1] Journal of Medicinal Chemistry, 2002, vol. 45, # 18, p. 3946 - 3952
[2] Patent: WO2013/33093, 2013, A1. Location in patent: Page/Page column 137; 138
[3] Angewandte Chemie - International Edition, 1997, vol. 37, # 19, p. 2708 - 2714
[4] Organic Letters, 2015, vol. 17, # 4, p. 1018 - 1021
[5] Journal of the American Chemical Society, 1978, vol. 100, p. 4555 - 4568

Methyl D-(-)-4-hydroxy-phenylglycinate(37763-23-8)Related Product Information

• CHLOROPHOSPHONAZO III
• DL-P-Hydroxyphenylglycine
• 4-Hydroxy-L-phenylglycine
• D-2-Phenylglycine
• 4-Aminophenylacetic acid
• 4-Hydroxy-D-(-)-2-phenylglycine
• Methyl acrylate
• Basic Violet 1
• 2-Hydroxyphenylacetic acid
• Methyl glycolate
• Acetonitrile
• Methanol
• METHYL 2-AMINO-2-(4-HYDROXYPHENYL)ACETATE
• Methylparaben
• Kresoxim-methyl
• 4-Hydroxybenzoic acid
• Paraquat dichloride
• 4-Hydroxybenzaldehyde