(s)-2-(Benzylamino)-3-hydroxypropanoic acid

Base Information

• Chemical Name: (s)-2-(Benzylamino)-3-hydroxypropanoic acid
• CAS No.: 17136-45-7
• Molecular Formula: C₁₀H₁₃NO₃
• Molecular Weight: 195.218
• Hs Code.: 2922509090
• European Community (EC) Number: 630-649-0
• DSSTox Substance ID: DTXSID10357456
• Nikkaji Number: J1.318.766E
• ChEMBL ID: CHEMBL4077985
• Mol file: 17136-45-7.mol

Synonyms:17136-45-7;bzl-ser-oh;L-N-Benzylserine;(s)-2-(benzylamino)-3-hydroxypropanoic acid;Benzyl-L-serine;(s)-(+)-n-benzylserine;(2S)-2-(benzylamino)-3-hydroxypropanoic acid;N-benzyl-L-serine;(S)-N-Benzylserine;L-Serine, N-(phenylmethyl)-;2-Benzylamino-3-hydroxy-propionic Acid;2(S)-Benzylamino-3-hydroxypropionic acid;N-benzylserine;MFCD00020417;N-benzyl-serine;(S)-2-BENZYLAMINO-3-HYDROXY-PROPIONIC ACID;(S)-N-Benzyl-serine;N-(phenylmethyl)-L-Serine;SCHEMBL1190016;CHEMBL4077985;DTXSID10357456;CTSBUHPWELFRGB-VIFPVBQESA-N;AKOS006273475;HY-W053678;CS-11087;CS-0046328;EN300-7323172;A848399

Chemical Property of (s)-2-(Benzylamino)-3-hydroxypropanoic acid

Chemical Property:

• Vapor Pressure: 2.63E-07mmHg at 25°C
• Melting Point: 223-225?C
• Refractive Index: 1.574
• Boiling Point: 405.6 °C at 760 mmHg
• PKA: 2.16±0.10(Predicted)
• Flash Point: 199.1 °C
• PSA: 69.56000
• Density: 1.246 g/cm³
• LogP: 0.61260
• Storage Temp.: 2-8°C
• Solubility.: DMSO
• XLogP3: -1
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 5
• Exact Mass: 195.08954328
• Heavy Atom Count: 14
• Complexity: 178

Purity/Quality:

≥98%,≥99%, ^*data from raw suppliers

(S)-(+)-N-Benzylserine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)CNC(CO)C(=O)O
• Isomeric SMILES: C1=CC=C(C=C1)CN[C@@H](CO)C(=O)O

Technology Process of (s)-2-(Benzylamino)-3-hydroxypropanoic acid

There total 19 articles about (s)-2-(Benzylamino)-3-hydroxypropanoic acid 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: 90.0%

(RS)-N-benzylserine (106910-76-3) → (S)-2-(benzylamino)-3-hydroxypropanoic acid (106910-76-3,106910-77-4,17136-45-7)

Guidance literature:

With C₂₄H₂₉CoN₂O₄; In dichloromethane; water; at 10 ℃; for 24h; optical yield given as %ee; Resolution of racemate;

DOI:10.1002/ejoc.200701101

Reference yield: 74.8%

L-serin (56-45-1,83245-15-2) + benzyl chloride (100-44-7) → (S)-2-(benzylamino)-3-hydroxypropanoic acid (106910-76-3,106910-77-4,17136-45-7)

Guidance literature:

With potassium carbonate; In water; at 20 ℃; for 25h;

DOI:10.1080/00397910008087240

Reference yield: 73.0%

L-serin (56-45-1,83245-15-2) + benzaldehyde (100-52-7) → (S)-2-(benzylamino)-3-hydroxypropanoic acid (106910-76-3,106910-77-4,17136-45-7)

Guidance literature:

With sodium cyanoborohydride; In methanol; for 18h; Ambient temperature;

DOI:10.1246/cl.1984.441

upstream raw materials:

L-serin

benzaldehyde

N-benzyl-L-serine methyl ester hydrochloride

benzyl chloride

Downstream raw materials:

Benzyl-((S)-2-oxo-oxetan-3-yl)-carbamic acid benzyl ester

(RS)-4-benzyl-5-oxomorpholine-3-carboxylic acid

(R)-(4-benzylmorpholin-3-yl)methanol hydrochloride

(3S)-5-oxo-N,4-bis(phenylmethyl)-3-morpholinecarboxamide

Refernces

• 1、 Borsari, Chiara,Rageot, Denise,Dall'Asen, Alix,Bohnacker, Thomas,Melone, Anna,Sele, Alexander M.,Jackson, Eileen,Langlois, Jean-Baptiste,Beaufils, Florent,Hebeisen, Paul,Fabbro, Doriano,Hillmann, Petra,Wymann, Matthias P.. "A Conformational Restriction Strategy for the Identification of a Highly Selective Pyrimido-pyrrolo-oxazine mTOR Inhibitor". . p. 8609 - 8630. Retrieved 2019/10/16.
• 2、 Gavai, Ashvinikumar V.,Fink, Brian E.,Fairfax, David J.,Martin, Gregory S.,Rossiter, Lana M.,Holst, Christian L.,Kim, Soong-Hoon,Leavitt, Kenneth J.,Mastalerz, Harold,Han, Wen-Ching,Norris, Derek,Goyal, Bindu,Swaminathan, Shankar,Patel, Bharat,Mathur, Arvind,Vyas, Dolatrai M.,Tokarski, John S.,Chiang, Yu,Oppenheimer, Simone,Hongjian, Zhang,Marathe, Punit,Fargnoli, Joseph,Lee, Francis Y.,Wong, Tai W.,Vite, Gregory D.. "Discovery and preclinical evaluation of [4-[[1-(3-fluorophenyl)methyl]-1H- indazol-5-ylamino]-5-methylpyrrolo[2,1-f][1,2,4]triazin-6-yl]carbamic acid, (3S)-3-morpholinylmethyl ester (BMS-599626), a selective and orally efficacious inhibitor of human epide". supporting information; experimental part. p. 6527 - 6530. Retrieved 2010/03/26.