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

Base Information

• Chemical Name: Methyl D-(-)-4-hydroxy-phenylglycinate
• CAS No.: 37763-23-8
• Molecular Formula: C9H11NO3
• Molecular Weight: 181.191
• Hs Code.: 2942000000
• European Community (EC) Number: 253-657-2,806-897-2
• DSSTox Substance ID: DTXSID00958815
• Nikkaji Number: J238.216D
• Mol file: 37763-23-8.mol

Synonyms:Benzeneaceticacid, α-amino-4-hydroxy-, methyl ester,(R)-;(R)-Methyl (4-hydroxyphenyl)glycinate;D-(4-Hydroxyphenyl)glycine methylester;D-p-Hydroxyphenylglycine methyl ester;Methyl D-(-)-α-amino-α-(4-hydroxyphenyl)acetate;Methyl (R)-amino(4-hydroxyphenyl)acetate;

Chemical Property of Methyl D-(-)-4-hydroxy-phenylglycinate

Chemical Property:

• Vapor Pressure: 6.03E-05mmHg at 25°C
• Refractive Index: 1.57
• Boiling Point: 335.7 °C at 760 mmHg
• PKA: 9.74±0.26(Predicted)
• Flash Point: 156.9 °C
• PSA: 72.55000
• Density: 1.248 g/cm³
• LogP: 1.26530
• Storage Temp.: Room Temperature
• Solubility.: DMSO (Slightly), Ethanol (Slightly, Sonicated), Methanol (Slightly)
• XLogP3: 0.5
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 181.07389321
• Heavy Atom Count: 13
• Complexity: 176

Purity/Quality:

99% ^*data from raw suppliers

MethylD-(-)-4-Hydroxy-phenylglycinate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC(=O)C(C1=CC=C(C=C1)O)N
• Uses: Methyl D-(-)-4-Hydroxy-phenylglycinate is useful for the synthesis (+)-radicamine B. Also, it is used for the preparation of amoxicillin.

Technology Process of Methyl D-(-)-4-hydroxy-phenylglycinate

There total 9 articles about Methyl D-(-)-4-hydroxy-phenylglycinate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 100.0%

methanol (67-56-1) + D-4-hydroxyphenylglycine (22818-40-2) → D-2-p-hydroxyphenylglycine methyl ester (37763-23-8)

Guidance literature:

With thionyl chloride; at 20 ℃; for 10h;

DOI:10.1021/jm020093q

Reference yield: 65.0%

methanol (67-56-1) + 4-((3R,5S)-2-oxo-5-phenyl-morpholin-3-yl)phenyl acetate (1327278-14-7) → D-4-hydroxyphenylglycine (22818-40-2) + D-2-p-hydroxyphenylglycine methyl ester (37763-23-8)

Guidance literature:

With 20 wt.% Pd(OH)2 on activated carbon; hydrogen; trifluoroacetic acid; In water; at 20 ℃; for 24h; under 3040.2 Torr;

DOI:10.1002/asia.201100452

Reference yield:

(R)-methyl 2-amino-2-(4-hydroxyphenyl)acetate (43189-12-4) → D-4-hydroxyphenylglycine (22818-40-2) + (S)-hydroxyphenylglycine (32462-30-9) + D-2-p-hydroxyphenylglycine methyl ester (37763-23-8) + (S)-methyl 2-amino-2-(4-hydroxyphenyl)acetate (26531-82-8)

Guidance literature:

With Bacillus licheniformis; sodium hydrogencarbonate; 1-ethyl-3-methylimidazolium acetate; In water; water-d2; at 30 ℃; for 3h;

DOI:10.1016/j.tetasy.2006.09.009

upstream raw materials:

methanol

D-4-hydroxyphenylglycine

Methyl 4-hydroxyphenylacetate

(R)-methyl 2-amino-2-(4-hydroxyphenyl)acetate

Downstream raw materials:

amoxicillin

(6R,7S)-7-[(R)-2-Amino-2-(4-hydroxy-phenyl)-acetylamino]-3-chloro-8-oxo-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid

(6R,7S)-7-[(R)-2-Amino-2-(4-hydroxy-phenyl)-acetylamino]-8-oxo-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid

(4S,6R,7S)-7-[(R)-2-Amino-2-(4-hydroxy-phenyl)-acetylamino]-4-methyl-8-oxo-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid

Refernces

• 1、 -. "APOPTOSIS-INDUCING AGENTS". Paragraph 295; 296. . Retrieved 2018/11/22.
• 2、 Fu, Shaomin,Yang, Honghao,Deng, Yuanfu,Jiang, Huanfeng,Zeng, Wei,Li, Guoqiang. "Copper(II)-catalyzed enantioselective intramolecular cyclization of N-alkenylureas". supporting information. p. 1018 - 1021. Retrieved 2015/03/30.