D-4-Hydroxyphenylglycine Methyl ester hydrochloride Chemical Properties

Melting point:

187-190 °C(lit.)

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

solubility 

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

form 

Solid

color 

White to Off-White

Stability:

Hygroscopic

InChI

InChI=1/C9H11NO3.ClH/c1-13-9(12)8(10)6-2-4-7(11)5-3-6;/h2-5,8,11H,10H2,1H3;1H/t8-;/s3

InChIKey

UYCKVJUNDXPDJH-JNODIIHCNA-N

SMILES

C1(=CC=C(O)C=C1)[C@@H](N)C(=O)OC.Cl |&1:7,r|

CAS DataBase Reference

57591-61-4

Safety Information

WGK Germany 

3

D-4-Hydroxyphenylglycine Methyl ester hydrochloride Usage And Synthesis

Chemical Properties

White to Off-White Solid

Uses

D-4-Hydroxyphenylglycine Methyl ester hydrochloride is used in the production of antiviral peptides and beta-lactam anti-biotics.

reaction suitability

reaction type: solution phase peptide synthesis

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. Upon completion of the reaction, the solvent was removed by concentration 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 × 15 mL) and dried to give the final D-p-hydroxyphenylglycine methyl ester hydrochloride (6.50 g, 100%) in white solid form with a melting point of 189-191 °C; [α]20D = -120.9 (c 1 , 1M HCl), literature value [α]25D = -121.1 (c 1 , 1M HCl); IR spectrum (KBr) νmax/cm-1: 3339 (broad peak, OH), 1740 (C=O), 1595 (aryl ring); 1H NMR (300 MHz, DMSO-d6) δ: 3.68 (3H, s, OCH3), 5.11 (1H, s, CH), 6.80 (2H, d, J = 8.5 Hz. H), 7.25 (2H, d, J = 8.5 Hz, aryl H), 8.70 (3H, broad peak, NH3+), 9.86 (1H, s, 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

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