| Identification | Back Directory | [Name]
Methyl D-(-)-4-hydroxy-phenylglycinate | [CAS]
37763-23-8 | [Synonyms]
Δ3-Flomoxef sodium
D- methyl p-hydroxyphenylglycine
METHYL DL-4-HYDROXYPHENYLGLYCINE HCL
Methyl D-(-)-4-hydroxy-phenylglycine
D-4-Hydroxyphenylglycine methyl ester
METHYL D-(-)-4-HYDROXY-PHENYLGLYCINATE
4-Hydroxy-D-phenylglycine methyl ester
methyl (R)-amino(4-hydroxyphenyl)acetate
(R)-α-(p-Hydroxyphenyl)glycine methyl ester
Methyl D-(-)-4-hydroxyphenylglycinate, 95+%
(S)-Methyl 2-aMino-2-(4-hydroxyphenyl)acetate
D-(-)-|á-P-HYDROXY PHENYLGLYCINE METHYL ESTER
Methyl (R)-2-amino-2-(4-hydroxyphenyl)acetate
D-(-)-alpha-p-Hydroxy-phenylglycine methyl ester
Methyl D-(-)-4-hydroxy-phenylglycinate USP/EP/BP
D(-) Alpha Parahydroxy Phenylglycine Methyl Ester
(R)-Amino(4-hydroxyphenyl)acetic acid methyl ester
2-amino-2-(4-hydroxyphenyl)acetic acid methyl ester
Benzeneacetic acid, α-aMino-4-hydroxy-, Methyl ester,(aR)-
Benzeneacetic acid, a-amino-4-hydroxy-, methyl ester, (aR)-
Benzeneacetic acid, α-amino-4-hydroxy-, methyl ester, (αR)-
Cefadroxil Impurity 1 (Methyl (2R)-2-Amino-2-(4-Hydroxyphenyl)acetate)
PHPGMe Methyl D-(-)4-hydroxy-phenylglycinate | [EINECS(EC#)]
253-657-2 | [Molecular Formula]
C9H11NO3 | [MDL Number]
MFCD09038793 | [MOL File]
37763-23-8.mol | [Molecular Weight]
181.19 |
| Chemical Properties | Back Directory | [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 |
| Hazard Information | Back Directory | [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]
Nonflammable | [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 |
|
|