N-[(Benzyloxy)carbonyl]-L-alanine

Base Information

• Chemical Name: N-[(Benzyloxy)carbonyl]-L-alanine
• CAS No.: 1142-20-7
• Molecular Formula: C11H13NO4
• Molecular Weight: 223.229
• Hs Code.: DERIVATION
• European Community (EC) Number: 214-532-8
• DSSTox Substance ID: DTXSID40150674
• Nikkaji Number: J80.198D
• Wikidata: Q27095370
• Metabolomics Workbench ID: 149070
• ChEMBL ID: CHEMBL1231234
• Mol file: 1142-20-7.mol

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

Chemical Property of N-[(Benzyloxy)carbonyl]-L-alanine

Chemical Property:

• Appearance/Colour: white powder
• Vapor Pressure: 7.05E-08mmHg at 25°C
• Melting Point: 82-84 °C
• Refractive Index: -14.5 ° (C=2, AcOH)
• Boiling Point: 422.1 °C at 760 mmHg
• PKA: 4.00±0.10(Predicted)
• Flash Point: 209.1 °C
• PSA: 75.63000
• Density: 1.246 g/cm³
• LogP: 1.77680
• Storage Temp.: 0-6°C
• Solubility.: Chloroform (Slightly), Methanol (Slightly)
• 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:

99% ^*data from raw suppliers

Z-L-Alanine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 20/21/22-36/37/38
• Safety Statements: 22-24/25-36-26

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C(=O)O)NC(=O)OCC1=CC=CC=C1
• Isomeric SMILES: C[C@@H](C(=O)O)NC(=O)OCC1=CC=CC=C1
• Uses: N-Benzyloxycarbonyl-L-alanine is an intermediate in the synthesis of Perindopril (P287500), an angiotensin-converting enzyme (ACE) inhibitor. Antihypertensive.

Technology Process of N-[(Benzyloxy)carbonyl]-L-alanine

There total 108 articles about N-[(Benzyloxy)carbonyl]-L-alanine 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%

L-alanin (56-41-7,25191-17-7,18875-37-1) + benzyl chloroformate (501-53-1,94274-21-2) → N-Cbz-Ala (1142-20-7)

Guidance literature:

With sodium hydroxide; In water; at 0 - 20 ℃;

DOI:10.1128/AAC.01152-16

Reference yield: 100.0%

N-benzyloxycarbonyl-L-alanate de desyle → N-Cbz-Ala (1142-20-7)

Guidance literature:

With potassium phosphate; tris(2,2-bipyridine)ruthenium(II) hexafluorophosphate; ascorbic acid; In water; acetonitrile; at 20 ℃; for 1h; Irradiation;

DOI:10.1021/acscatal.7b02117

Reference yield: 100.0%

Z-L-Ala benzyl ester (88718-12-1) → N-Cbz-Ala (1142-20-7)

Guidance literature:

With 4-methyl-morpholine; In water; acetonitrile; at 30 ℃; for 48h; under 7500600 Torr;

DOI:10.1021/jo00020a001

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:

L-Alanine methyl ester

3-benzyloxycarbonyl-4-methyloxazolidin-5-one

Cbz-HN-Ala-Ala

N-(N-benzyloxycarbonyl-L-alanyl)-N'-o-toluoyl-hydrazine

Refernces

• 1、 Yamamoto, Tomoya,Chang, Tsung-Che,Tanaka, Katsunori. "Epoc group: Transformable protecting group with gold(iii)-catalyzed fluorene formation". . p. 10703 - 10709. Retrieved 2021.
• 2、 Luong, Hoa,Luss-Lusis, Eduard,Tanoury, Gerald J.,Nugent, William A.. "Improvement in the one-carbon chain extension of esters with dimethylsulfoxonium methylide". . p. 4238 - 4241. Retrieved 2013.
• 3、 Das, Apurba K.,Bose, Partha Pratim,Drew, Michael G.B.,Banerjee, Arindam. "The role of protecting groups in the formation of organogels through a nano-fibrillar network formed by self-assembling terminally protected tripeptides". . p. 7432 - 7442. Retrieved 2007.
• 4、 Namikoshi, Michio,Kundu, Bijoy,Rinehart, Kenneth L.. "Use of Tetrabutylammonium Fluoride as a Facile Deprotecting Reagent for 4-Nitrobenzyl, 2,2,2-Trichloroethyl, and Phenacyl Esters of Amino Acids". . p. 5464 - 5466. Retrieved 1991.
• 5、 Harrington et al.. "". . p. 168,169. Retrieved 1973.
• 6、 Albat, Dominik,Neud?rfl, J?rg-Martin,Schmalz, Hans-Günther. "A General Stereocontrolled Synthesis of Opines through Asymmetric Pd-Catalyzed N-Allylation of Amino Acid Esters". supporting information. p. 2099 - 2102. Retrieved 2021/07/22.
• 7、 Cheng, Jiang-Tao,Dong, Xiao-Yang,Gu, Qiang-Shuai,Li, Zhong-Liang,Liu, Juan,Liu, Xin-Yuan,Luan, Cheng,Wang, Fu-Li,Wang, Li-Lei,Yang, Ning-Yuan,Zhang, Yu-Feng. "Enantioconvergent Cu-Catalyzed Radical C-N Coupling of Racemic Secondary Alkyl Halides to Access α-Chiral Primary Amines". supporting information. p. 15413 - 15419. Retrieved 2021/09/30.