|
|
| | D-4-Hydroxyphenylglycine Methyl ester hydrochloride Basic information |
| Product Name: | D-4-Hydroxyphenylglycine Methyl ester hydrochloride | | Synonyms: | Methyl (R)-2-Amino-2-(4-hydroxyphenyl)acetate Hydrochloride;Amoxicillin Impurity 17;D(-)4-HYDROXY-ALPA-PHENYL GLYCINE METHYL ESTER HYDROCHLORIDE;D-4-Hydroxyphenylglycine methyl ester HCl;D-(-)-P-HYDROXYPHENYLGLYCINE METHYL ESTE;D-4-Hydroxyphenylglycine methyl ester hydrochloride;D-p-hydroxyphenyl-glycine methyl hydrochloride;(R)-Amino-(4-hydroxyphenyl)acetic acid methyl ester hydrochloride | | CAS: | 57591-61-4 | | MF: | C9H12ClNO3 | | MW: | 217.65 | | EINECS: | 1308068-626-2 | | Product Categories: | bc0001 | | Mol File: | 57591-61-4.mol |  |
| | 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 |
| | 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 |
| | D-4-Hydroxyphenylglycine Methyl ester hydrochloride Preparation Products And Raw materials |
|