(R)-Methyl 2-(benzylamino)-3-hydroxypropanoate

Base Information

• Chemical Name: (R)-Methyl 2-(benzylamino)-3-hydroxypropanoate
• CAS No.: 131110-76-4
• Molecular Formula: C₁₁H₁₅NO₃
• Molecular Weight: 209.245
• Hs Code.: 2922509090
• DSSTox Substance ID: DTXSID10453861
• Nikkaji Number: J1.439.231I
• Wikidata: Q82275130
• Mol file: 131110-76-4.mol

Synonyms:131110-76-4;D-N-Benzylserine Methyl Ester;(R)-Methyl 2-(benzylamino)-3-hydroxypropanoate;METHYL (R)-2-(BENZYLAMINO)-3-HYDROXYPROPANOATE;n-benzyl-d-serine methyl ester;D-Serine, N-(phenylmethyl)-, methyl ester;methyl N-benzyl-D-serinate;METHYL (2R)-2-(BENZYLAMINO)-3-HYDROXYPROPANOATE;D-N-BenzylserineMethylEster;MFCD12198843;Methyl benzyl-D-serinate;SCHEMBL304265;DTXSID10453861;GMZGWPPEZCREPP-SNVBAGLBSA-N;Methyl N-(phenylmethyl)-D-serinate;AKOS015888178;AS-31565;CS-0146699;EN300-7003360

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

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Boiling Point: 351.127oC at 760 mmHg
• Flash Point: 166.156oC
• PSA: 58.56000
• Density: 1.15g/cm3
• LogP: 0.70100
• Storage Temp.: Keep in dark place,Sealed in dry,Store in freezer, under -20°C
• 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

Methyl(r)-2-(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
• Isomeric SMILES: COC(=O)[C@@H](CO)NCC1=CC=CC=C1

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

There total 6 articles about (R)-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:

D-serine methyl ester (2104-89-4,2788-84-3,24184-43-8) + benzaldehyde (100-52-7) → methyl (2R)-2-(benzylamino)-3-hydroxypropanoate (123639-56-5,131110-76-4,144001-42-3)

Guidance literature:

D-serine methyl ester; benzaldehyde; With sodium cyanoborohydride; In methanol;

With methanol; water; sodium hydrogencarbonate;

Reference yield:

(R)-3-Hydroxy-2-{[1-phenyl-meth-(E)-ylidene]-amino}-propionic acid methyl ester (40216-75-9) → methyl (2R)-2-(benzylamino)-3-hydroxypropanoate (123639-56-5,131110-76-4,144001-42-3)

Guidance literature:

With sodium tetrahydroborate;

DOI:10.1016/S0040-4039(00)97768-2

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:

(R)-3-benzyl-2,2-dimethyl-4-oxazolidinecarboxylic acid methyl ester

methyl (2R)-2-(benzylamino)-3-{[tert-butyl(dimethyl)silyl]oxy}propanoate

(7R,9aR)-7-(hydroxymethyl)-8-(phenylmethyl)hexahydropyrazino[2,1-c][1,4]oxazine-6,9-dione

4-allyl 1-[(2R)-2-(benzylamino)-3-methoxy-3-oxopropyl] N-(tert-butoxycarbonyl)-L-aspartate

Refernces

• 1、 -. "BTK INHIBITORS". Page/Page column 93. . Retrieved 2016/07/27.
• 2、 Xu, Jing,Caro-Diaz, Eduardo J. E.,Trzoss, Lynnie,Theodorakis, Emmanuel A.. "Nature-inspired total synthesis of (-)-fusarisetin A". supporting information; experimental part. p. 5072 - 5075. Retrieved 2012/05/07.