Methyl N-[(benzyloxy)carbonyl]valinate

Base Information

• Chemical Name: Methyl N-[(benzyloxy)carbonyl]valinate
• CAS No.: 134306-34-6
• Molecular Formula: C14H19NO4
• Molecular Weight: 265.309
• DSSTox Substance ID: DTXSID00506512
• Mol file: 134306-34-6.mol

Synonyms:134306-34-6;3-methyl-2-(phenylmethoxycarbonylamino)butanoic acid methyl ester;METHYL (2R)-2-{[(BENZYLOXY)CARBONYL]AMINO}-3-METHYLBUTANOATE;Methyl N-[(benzyloxy)carbonyl]valinate;SCHEMBL10535596;DTXSID00506512;AKOS008906828

Chemical Property of Methyl N-[(benzyloxy)carbonyl]valinate

Chemical Property:

• XLogP3: 2.7
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 7
• Exact Mass: 265.13140809
• Heavy Atom Count: 19
• Complexity: 298

Purity/Quality:

99.90% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

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

Technology Process of Methyl N-[(benzyloxy)carbonyl]valinate

There total 9 articles about Methyl N-[(benzyloxy)carbonyl]valinate 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: 95.0%

L-valine methyl ester (4070-48-8) + Carbonic acid benzyl ester 6-trifluoromethyl-benzotriazol-1-yl ester (112380-58-2) → N-(Benzyloxycarbonyl)valine methyl ester (134306-34-6)

Guidance literature:

In acetonitrile; for 24h; Ambient temperature;

DOI:10.1055/s-1987-28002

Reference yield: 85.0%

tetrabutyl ammonium fluoride (429-41-4) + benzyl bromide (100-39-0) → N-(Benzyloxycarbonyl)valine methyl ester (134306-34-6)

Guidance literature:

In tetrahydrofuran; hexane;

Reference yield: 84.0%

methanol (67-56-1) + (2S,5R,3E)-2-(Benzyloxymethoxy)-6-methyl-5-(benzyloxycarbonylamino)hept-3-ene (154674-66-5) → N-(Benzyloxycarbonyl)valine methyl ester (134306-34-6) + Methyl (S)-2-benzyloxymethoxypropanoate (170985-87-2)

Guidance literature:

(2S,5R,3E)-2-(Benzyloxymethoxy)-6-methyl-5-(benzyloxycarbonylamino)hept-3-ene; With ozone; In methanol; at -78 ℃; for 0.333333h;

With dimethylsulfide; In methanol; at -78 - 20 ℃; for 1h;

methanol; With water; bromine; sodium hydrogencarbonate; at 20 ℃; Title compound not separated from byproducts;

DOI:10.1039/a905772b

upstream raw materials:

diazomethane

N-benzyloxycarbonylvaline

L-valine methyl ester

Carbonic acid benzyl ester 6-trifluoromethyl-benzotriazol-1-yl ester

Downstream raw materials:

N-Boc-valine methyl ester

(+/-)-DL-valine-(cis-2-hydroxy-cyclohexylamide)

N-benzyloxycarbonyl-DL-valine hydrazide

(+/-)-N-benzyloxycarbonyl-DL-valine-(cis-2-hydroxy-cyclohexylamide)

Refernces

• 1、 Qian, Xiaoxia,Liang, Gui-Bai,Feng, Dennis,Fisher, Michael,Crumley, Tami,Rattray, Sandra,Dulski, Paula M.,Gurnett, Anne,Leavitt, Penny Sue,Liberator, Paul A.,Misura, Andrew S.,Samaras, Samantha,Tamas, Tamas,Schmatz, Dennis M.,Wyvratt, Matthew,Biftu, Tesfaye. "Synthesis and SAR Studies of diarylpyrrole anticoccidial agents". . p. 2817 - 2821. Retrieved 2007/10/03.
• 2、 -. "Tertiary-butyldimethylsilyl carbamate derivative and process for producing the same". . . Retrieved 2008/06/13.