Methyl 2-(benzylamino)-3-hydroxypropanoate

Base Information

• Chemical Name: Methyl 2-(benzylamino)-3-hydroxypropanoate
• CAS No.: 144001-42-3
• Molecular Formula: C11H15NO3
• Molecular Weight: 209.245
• Hs Code.: 2922509090
• DSSTox Substance ID: DTXSID60455815
• Mol file: 144001-42-3.mol

Synonyms:Methyl 2-(benzylamino)-3-hydroxypropanoate;144001-42-3;N-Benzyl-DL-serine methyl ester;MFCD18651713;Methyl (S)-2-(Benzylamino)-3-hydroxypropanoate;MFCD07367716;MFCD12198843;SCHEMBL14636601;DTXSID60455815;AKOS015888299;CS-W003903;HY-W003903;AC-23486;DS-13182;Methyl2-(benzylamino)-3-hydroxypropanoate;SY005128;SY005134;SY013175;FT-0663039;FT-0727251;FT-0771732;EN300-7044360;A884840;A890662

Chemical Property of Methyl 2-(benzylamino)-3-hydroxypropanoate

Chemical Property:

• Boiling Point: 351.1±32.0 °C(Predicted)
• PKA: 13.94±0.10(Predicted)
• PSA: 58.56000
• Density: 1.149±0.06 g/cm3(Predicted)
• LogP: 0.70100
• Storage Temp.: 2-8°C(protect from light)
• XLogP3: 1.6
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 6
• Exact Mass: 209.10519334
• Heavy Atom Count: 15
• Complexity: 190

Purity/Quality:

98%min ^*data from raw suppliers

Methyl2-(Benzylamino)-3-hydroxypropanoate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC(=O)C(CO)NCC1=CC=CC=C1

Technology Process of Methyl 2-(benzylamino)-3-hydroxypropanoate

There total 12 articles about Methyl 2-(benzylamino)-3-hydroxypropanoate 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: 99.0%

R-(-)-serine methyl ester hydrochloride (5874-57-7) + benzaldehyde (100-52-7) → methyl (2R)-2-(benzylamino)-3-hydroxypropanoate (123639-56-5,131110-76-4,144001-42-3)

Guidance literature:

R-(-)-serine methyl ester hydrochloride; benzaldehyde; With magnesium sulfate; triethylamine; In dichloromethane; at 20 ℃; for 24h;

With sodium tetrahydroborate; In methanol; at 0 ℃; for 3h; Further stages.;

DOI:10.1021/ol701733u

Reference yield: 81.0%

Ser-OMe (2104-89-4,2788-84-3,24184-43-8) + benzyl bromide (100-39-0) → methyl 2-(benzylamino)-3-hydroxypropanoate (144001-42-3)

Guidance literature:

With potassium carbonate; In N,N-dimethyl-formamide; at 50 ℃; for 8h;

DOI:10.1016/j.tetlet.2007.12.008

Reference yield: 60.0%

benzyl bromide (100-39-0) + methyl 2-amino-3-hydroxypropanoate hydrochloride (5619-04-5) → methyl 2-(benzylamino)-3-hydroxypropanoate (144001-42-3)

Guidance literature:

With potassium carbonate; In N,N-dimethyl-formamide; at 55 ℃; for 16h; Inert atmosphere;

DOI:10.1002/ejoc.201900300

upstream raw materials:

(R)-3-Hydroxy-2-{[1-phenyl-meth-(E)-ylidene]-amino}-propionic acid methyl ester

R-(-)-serine methyl ester hydrochloride

benzaldehyde

D-serine methyl ester

Downstream raw materials:

methyl 2-(N-benzyl-2,2-dichloroethanamido)propenoate

methyl 2-(benzyl(methyl)amino)-3-hydroxypropanoate

C₁₆H₂₄N₂O₇S

N-benzyl-N-carbobenzyloxy-O-tert-butyldimethylsilyl-D-serinal

Refernces

• 1、 Chen, Shi-Lu,He, Jin,Hong, Yu,Li, Jin-Heng,Liu, Jian,Liu, Ting,Tang, Shi,Wang, Shuo-Wen,Xu, Zhen-Hua,Yu, Jian. "Radical 1,4-Aryl Migration Enabled Remote Cross-Electrophile Coupling of α-Amino-β-Bromo Acid Esters with Aryl Bromides". supporting information. p. 21360 - 21367. Retrieved 2021/08/23.
• 2、 Morlot, Marine,Gourand, Fabienne,Perrio, Cécile. "Deoxyradiofluorination Reaction from β-Hydroxy-α-aminoesters: an Entry to [18F]Fluoroaminoesters under Mild Conditions". . p. 3751 - 3762. Retrieved 2019/06/24.