2-(((Benzyloxy)carbonyl)amino)propanoic acid

Base Information

• Chemical Name: 2-(((Benzyloxy)carbonyl)amino)propanoic acid
• CAS No.: 4132-86-9
• Molecular Formula: C₁₁H₁₃NO₄
• Molecular Weight: 223.229
• Hs Code.: 29242990
• European Community (EC) Number: 223-953-6
• NSC Number: 523825,156978,88469,27684
• DSSTox Substance ID: DTXSID701302668
• Nikkaji Number: J154.032G
• Mol file: 4132-86-9.mol

Synonyms:Cbz-Ala;Cbz-alanine;N-(carbobenzoxy)alanine;N-benzoxycarbonyl-alanine;N-benzyloxycarbonylalanine;N-carbobenzyloxyalanine

Chemical Property of 2-(((Benzyloxy)carbonyl)amino)propanoic acid

Chemical Property:

• Appearance/Colour: white powder
• Vapor Pressure: 7.05E-08mmHg at 25°C
• Melting Point: 112-113 °C(lit.)
• Refractive Index: 1.4960 (estimate)
• Boiling Point: 422.1 °C at 760 mmHg
• PKA: 4.00±0.10(Predicted)
• Flash Point: 209.1 °C
• PSA: 75.63000
• Density: 1.247 g/cm³
• LogP: 1.77680
• Storage Temp.: −20°C
• Solubility.: almost transparency in Methanol
• XLogP3: 1.4
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 5
• Exact Mass: 223.08445790
• Heavy Atom Count: 16
• Complexity: 248

Purity/Quality:

MIN 98.5% ^*data from raw suppliers

Z-DL-ALA-OH ^*data from reagent suppliers

Safty Information:

• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C(=O)O)NC(=O)OCC1=CC=CC=C1

Technology Process of 2-(((Benzyloxy)carbonyl)amino)propanoic acid

There total 7 articles about 2-(((Benzyloxy)carbonyl)amino)propanoic 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: 98.0%

3,5-dimethyl-pyrazole-1-carboxylic acid benzyl ester (91806-74-5) + rac-Ala-OH (302-72-7,25191-17-7,18875-37-1) → N-benzyloxycarbonylalanine (4132-86-9,26607-51-2,1142-20-7)

Guidance literature:

With sodium hydride; In N,N-dimethyl-formamide; at -5 ℃; for 5h;

DOI:10.1016/S0040-4020(98)00947-8

Reference yield: 96.0%

N-Benzyloxycarbonyl-D,L-alanine 4-nitrobenzyl ester (247089-50-5) → N-benzyloxycarbonylalanine (4132-86-9,26607-51-2,1142-20-7)

Guidance literature:

With indium; ammonium chloride; In ethanol; for 18h; Heating;

DOI:10.1055/s-1999-2904

Reference yield: 95.0%

benzyl chloroformate (501-53-1,94274-21-2) + rac-Ala-OH (302-72-7,25191-17-7,18875-37-1) → N-benzyloxycarbonylalanine (4132-86-9,26607-51-2,1142-20-7)

Guidance literature:

With sodium carbonate; In tetrahydrofuran; water; at 0 - 20 ℃; for 2h;

DOI:10.1016/j.tetlet.2012.05.057

upstream raw materials:

benzyl chloroformate

rac-Ala-OH

2-Benzyloxycarbonylamino-propionic acid 2,2,2-trifluoro-ethyl ester

3,5-dimethyl-pyrazole-1-carboxylic acid benzyl ester

Downstream raw materials:

Cbz-HN-Ala-Ala

N-(N-benzyloxycarbonyl-alanyl)-N'-salicyloyl-hydrazine

N-benzyloxycarbonyl-alanine benzyl ester

N-benzyloxycarbonyl-thioalanine S-(4-nitro-phenyl ester)

Refernces

• 1、 Slack, Eric D.,Gabriel, Christopher M.,Lipshutz, Bruce H.. "A palladium nanoparticle-nanomicelle combination for the stereo-selective semihydrogenation of alkynes in water at room temperature". supporting information. p. 14051 - 14054. Retrieved 2015/02/19.
• 2、 Miyazawa, Toshifumi,Mio, Motoe,Watanabe, Yuko,Yamada, Takashi. "Resolution of non-proteinogenic amino acids via microbial lipase-catalyzed enantioselective transesterification". . p. 219 - 224. Retrieved 2008/09/20.