Boc-N-methyl-L-leucine

Base Information

• Chemical Name: Boc-N-methyl-L-leucine
• CAS No.: 53363-89-6
• Molecular Formula: C12H23NO4
• Molecular Weight: 245.319
• Hs Code.: 2924 19 00
• European Community (EC) Number: 834-864-2
• Nikkaji Number: J943.978A
• Mol file: 53363-89-6.mol

Synonyms:Boc-N-methyl-L-leucine;53363-89-6;Boc-N-Me-Leu-OH;Boc-MeLeu-OH;N-(tert-butoxycarbonyl)-N-methyl-L-leucine;L-Leucine, N-[(1,1-dimethylethoxy)carbonyl]-N-methyl-;N-alpha-t-Butyloxycarbonyl-N-alpha-methyl-L-leucine;N-boc-N-methyl-d-leucine;(S)-2-(tert-butoxycarbonyl(methyl)amino)-4-methylpentanoic acid;(2S)-2-{[(tert-butoxy)carbonyl](methyl)amino}-4-methylpentanoic acid;Boc-L-MeLeu-OH;Boc-Nalpha-methyl-L-leucine;BocMeLeuOH;N-Boc-N-methylleucine;N-Methyl-N-Boc-L-Leucine;SCHEMBL38056;YXJFAOXATCRIKU-VIFPVBQESA-N;AMY22589;t-butoxycarbonyl-N-methyl-L-leucine;2-((TERT-BUTOXYCARBONYL)(METHYL)AMINO)-4-METHYLPENTANOIC ACID;MFCD00038522;AKOS015836698;AKOS015908789;N-methyl-tert-butoxycarbonyl-L-leucine;t-Butyloxycarbonyl-N-Methyl-L-Leucine;CS-W010250;FD21863;HY-W009534;N-tert-Butoxycarbonyl-N-methyl-L-leucine;AC-31990;DS-14206;EN300-370798;A829541;Boc-N-Me-Leu-OH, >=99.0% (sum of enantiomers, TLC);(2S)-2-[tert-butoxycarbonyl(methyl)amino]-4-methyl-pentanoic acid

Chemical Property of Boc-N-methyl-L-leucine

Chemical Property:

• Appearance/Colour: White powder
• Vapor Pressure: 1.86E-05mmHg at 25°C
• Melting Point: 55-60 °C
• Refractive Index: 1.466
• Boiling Point: 338.2 °C at 760 mmHg
• PKA: 4.04±0.21(Predicted)
• Flash Point: 158.3 °C
• PSA: 66.84000
• Density: 1.053 g/cm³
• LogP: 2.35260
• Storage Temp.: Store at RT.
• XLogP3: 2.4
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 6
• Exact Mass: 245.16270821
• Heavy Atom Count: 17
• Complexity: 281

Purity/Quality:

99% ^*data from raw suppliers

Boc-N-methyl-L-leucine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)CC(C(=O)O)N(C)C(=O)OC(C)(C)C
• Isomeric SMILES: CC(C)C[C@@H](C(=O)O)N(C)C(=O)OC(C)(C)C
• Description: Boc-N-methyl-L-leucine is the BOC (tert-butyloxycarbonyl) protected N-methylated leucine. The N-methylated amino acid is quite useful in the peptide synthesis, giving a lot of improved properties to peptide. Studies have shown that peptide containing N-methylated amino acids obtain increased proteolytic stability, increased membrane permeability, and altered conformation. The effects of N-methylated amino acids are quite important in the development of therapeutic peptide compound as well as in the assay of biological activity of some modified peptides. BOC group can be easily removed by treatment with strong acids such as trifluoroacetic acid.
• Uses: Boc-N-methyl-L-leucine, is an amino acid building block used in peptide synthesis. With a growing peptide drug market the fast, reliable synthesis of peptides is of great importance.

Technology Process of Boc-N-methyl-L-leucine

There total 14 articles about Boc-N-methyl-L-leucine 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%

N-tert-butoxycarbonyl-L-leucine (13139-15-6,53296-34-7) + methyl iodide (74-88-4) → N-t-butoxycarbonyl-N-methyl-L-leucine (53363-89-6)

Guidance literature:

N-tert-butoxycarbonyl-L-leucine; With sodium hydride; In tetrahydrofuran; mineral oil; at 0 ℃; for 0.5h; Inert atmosphere;

methyl iodide; In N,N-dimethyl-formamide; mineral oil; at 0 - 20 ℃; for 4.5h; Inert atmosphere;

DOI:10.1016/j.tetlet.2014.09.047

Reference yield: 94.0%

(4S)-N-(tert-butyloxycarbonyl)-4-isobutyl-1,3-oxazolidin-5-one (172096-97-8) → N-t-butoxycarbonyl-N-methyl-L-leucine (53363-89-6)

Guidance literature:

With chloro-trimethyl-silane; sodium cyanoborohydride; In acetonitrile; for 0.166667h; Ambient temperature;

DOI:10.1246/cl.1999.299

Reference yield: 92.0%

N-tert-butoxycarbonyl-L-leucine (13139-15-6,53296-34-7) + dimethyl sulfate (77-78-1) → N-t-butoxycarbonyl-N-methyl-L-leucine (53363-89-6)

Guidance literature:

With water; sodium hydride; In tetrahydrofuran; at 17 - 20 ℃; for 1h;

DOI:10.1021/ol0268440

upstream raw materials:

N-tert-butoxycarbonyl-L-leucine

methyl iodide

dimethyl sulfate

(4S)-N-(tert-butyloxycarbonyl)-4-isobutyl-1,3-oxazolidin-5-one

Downstream raw materials:

((S)-1-{[2-(4-Benzyloxy-phenyl)-ethyl]-methyl-carbamoyl}-3-methyl-butyl)-methyl-carbamic acid tert-butyl ester

N-(tert-butoxycarbonyl)-N-methyl-L-leucyl-L-alanine benzyl ester

N-methyl-L-leucine benzyl ester

benzyl N-Boc-N-methyl-L-leucyl-3-phenyl-D-lactate

Refernces

• 1、 -. "Preparation method of N-trimethyl silicon ethoxycarbonyl-N-methyl-L/D-leucine". Paragraph 0078; 0081; 0096; 0099. . Retrieved 2021/06/02.
• 2、 -. "ENDOPARASITIC DEPSIPEPTIDES". Page/Page column 44; 45. . Retrieved 2019/11/28.