BOC-DL-PHENYLALANINE METHYL ESTER

Base Information

• Chemical Name: BOC-DL-PHENYLALANINE METHYL ESTER
• CAS No.: 19901-50-9
• Molecular Formula: C₁₅H₂₁NO₄
• Molecular Weight: 279.336
• DSSTox Substance ID: DTXSID20396396
• Nikkaji Number: J1.400.831D
• Mol file: 19901-50-9.mol

Synonyms:BOC-DL-PHENYLALANINE METHYL ESTER;N-Boc phenylalanine methyl ester;MeO-D-Phe-NHBoc;N-Boc-D-phenylalanine methyl ester;N-tert-butoxycarbonyl-D-phenylalanine methyl ester;Boc-D-Phe-OMe;

Chemical Property of BOC-DL-PHENYLALANINE METHYL ESTER

Chemical Property:

• PSA: 68.12000
• LogP: 2.49980
• XLogP3: 2.3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 7
• Exact Mass: 279.14705815
• Heavy Atom Count: 20
• Complexity: 329

Purity/Quality:

98%Min ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)NC(CC1=CC=CC=C1)C(=O)OC

Technology Process of BOC-DL-PHENYLALANINE METHYL ESTER

There total 68 articles about BOC-DL-PHENYLALANINE METHYL ESTER 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%

methanol (67-56-1) + Boc-D-Phe-OH (18942-49-9) → methyl (2R)-2-(t-butoxycarbonylamino)-3-phenylpropionate (19901-50-9,51987-73-6,77119-84-7)

Guidance literature:

With diazomethyl-trimethyl-silane; In benzene; Inert atmosphere;

DOI:10.1016/j.tetlet.2014.10.089

Reference yield: 99.0%

di-tert-butyl dicarbonate (24424-99-5) + methyl (2S)-2-amino-3-phenylpropanoate hydrochloride (7524-50-7) → methyl 2-tert-butoxycarbonylamino-3-phenylpropanoate (51987-73-6,77119-84-7,19901-50-9)

Guidance literature:

With triethylamine; In dichloromethane; at 20 ℃; for 48h;

Reference yield: 96.0%

N-(tert-butoxycarbonyl)glycine methyl ester (31954-27-5) + benzyl bromide (100-39-0) → methyl 2-tert-butoxycarbonylamino-3-phenylpropanoate (51987-73-6,77119-84-7,19901-50-9)

Guidance literature:

N-(tert-butoxycarbonyl)glycine methyl ester; With quinuclidine-N-oxide; tert.-butyl lithium; In tetrahydrofuran; hexanes; at 0 ℃; Inert atmosphere;

benzyl bromide; In tetrahydrofuran; hexanes; at 0 - 20 ℃; for 13h; Inert atmosphere;

DOI:10.1016/j.tetlet.2009.03.105

upstream raw materials:

benzyl bromide

acetyloxy[[(1,1-dimethylethoxy)carbonyl]amino]acetic acid methyl ester

N-(tert-butoxycarbonyl)glycine methyl ester

toluene

Downstream raw materials:

(D,L)-3-(4-nitrobenzyl)-5-(2-phenyl-1-tert-butyloxycarbonylaminoethyl)-1,2,4-oxadiazole

(D,L)-3-(3-methoxybenzyl)-5-(2-phenyl-1-tert-butyloxycarbonylaminoethyl)-1,2,4-oxadiazole

(S)-[3-Chloro-2-oxo-1-(phenylmethyl)propyl]-carbamic acid,1,1-dimethylethyl ester

C₄₈H₅₅N₉O₈S₂

Refernces

• 1、 Le Manach, Claire,Dam, Jean,Woodland, John G.,Kaur, Gurminder,Khonde, Lutete P.,Brunschwig, Christel,Njoroge, Mathew,Wicht, Kathryn J.,Horatscheck, André,Paquet, Tanya,Boyle, Grant A.,Gibhard, Liezl,Taylor, Dale,Lawrence, Nina,Yeo, Tomas,Mok, Sachel,Eastman, Richard T.,Dorjsuren, Dorjbal,Talley, Daniel C.,Guo, Hui,Simeonov, Anton,Reader, Janette,Van Der Watt, Mari?tte,Erlank, Erica,Venter, Nelius,Zawada, Jacek W.,Aswat, Ayesha,Nardini, Luisa,Coetzer, Theresa L.,Lauterbach, Sonja B.,Bezuidenhout, Belinda C.,Theron, Anjo,Mancama, Dalu,Koekemoer, Lizette L.,Birkholtz, Lyn-Marie,Wittlin, Sergio,Delves, Michael,Ottilie, Sabine,Winzeler, Elizabeth A.,Smith, Dennis,Fidock, David A.,Street, Leslie J.,Basarab, Gregory S.,Duffy, James,Chibale, Kelly. "Identification and Profiling of a Novel Diazaspiro[3.4]octane Chemical Series Active against Multiple Stages of the Human Malaria Parasite Plasmodium falciparum and Optimization Efforts". supporting information. p. 2291 - 2309. Retrieved 2021/03/01.
• 2、 Constantin, Timothée,Juliá, Fabio,Leonori, Daniele,Regni, Alessio,Sheikh, Nadeem S.,Zanini, Margherita. "Aminoalkyl radicals as halogen-atom transfer agents for activation of alkyl and aryl halides". . p. 1021 - 1026. Retrieved 2020/03/10.