Fmoc-N-methyl-L-leucine

Base Information

• Chemical Name: Fmoc-N-methyl-L-leucine
• CAS No.: 103478-62-2
• Molecular Formula: C22H25NO4
• Molecular Weight: 367.445
• Hs Code.: 29242990
• European Community (EC) Number: 689-222-2
• DSSTox Substance ID: DTXSID70426778
• Nikkaji Number: J2.225.617C
• Wikidata: Q72478645
• Mol file: 103478-62-2.mol

Synonyms:Fmoc-N-Me-Leu-OH;103478-62-2;Fmoc-N-methyl-L-leucine;N-Fmoc-N-methyl-L-leucine;MFCD00151933;FMOC-MeLeu-OH;Fmoc-N-a-methyl-L-Leucine;L-Leucine, N-[(9H-fluoren-9-ylmethoxy)carbonyl]-N-methyl-;(2S)-2-[9H-fluoren-9-ylmethoxycarbonyl(methyl)amino]-4-methylpentanoic acid;(S)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)(methyl)amino)-4-methylpentanoic acid;(2S)-2-({[(9H-fluoren-9-yl)methoxy]carbonyl}(methyl)amino)-4-methylpentanoic acid;Fmoc-Nalpha-methyl-L-leucine;Fmoc-N-Me-L-Leu-OH;N-Methyl-N-Fmoc-L-Leu-OH;Fmoc-N-|A-methyl-L-Leucine;SCHEMBL1486163;DTXSID70426778;(2S)-2-[9H-fluoren-9-ylmethoxycarbonyl(methyl)amino]-4-methyl-pentanoic acid;AKOS015837125;AC-8569;AM81898;CS-W008558;FD21861;HY-W008558;MH-0721;(2S)-2-{[(9H-fluoren-9-ylmethoxy)carbonyl](methyl)amino}-4-methylpentanoic acid;F1028;M03367;EN300-1268400;A800747;Fmoc-N-Me-Leu-OH, >=99.0% (sum of enantiomers, HPLC);N-[(9H-fluoren-9-ylmethoxy)carbonyl]-N-methyl-L-Leucine;N-(((9H-Fluoren-9-yl)methoxy)carbonyl)-N-methyl-L-leucine;N-alpha-(9-Fluorenylmethyloxycarbonyl)-N-alpha-methyl-L-leucine

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

Chemical Property:

• Appearance/Colour: White powder
• Vapor Pressure: 2.25E-12mmHg at 25°C
• Melting Point: 113-116 °C
• Refractive Index: 1.581
• Boiling Point: 537.3 °C at 760 mmHg
• PKA: 3.93±0.21(Predicted)
• Flash Point: 278.7 °C
• PSA: 66.84000
• Density: 1.194 g/cm³
• LogP: 4.36660
• Storage Temp.: 2-8°C
• Water Solubility.: Slightly soluble in water.
• XLogP3: 4.6
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 7
• Exact Mass: 367.17835828
• Heavy Atom Count: 27
• Complexity: 512

Purity/Quality:

98% ^*data from raw suppliers

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

Safty Information:

• Safety Statements: 22-24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)CC(C(=O)O)N(C)C(=O)OCC1C2=CC=CC=C2C3=CC=CC=C13
• Isomeric SMILES: CC(C)C[C@@H](C(=O)O)N(C)C(=O)OCC1C2=CC=CC=C2C3=CC=CC=C13
• Uses: It is an important raw material and intermediate used in organic synthesis, pharmaceuticals, agrochemicals and dyestuff.

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

There total 8 articles about Fmoc-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-Fmoc-N-methyl-L-leucine benzhydryl ester (1220527-61-6) → N-(9-fluorenylmethoxycarbonyl)-N-methyl-L-leucine (103478-62-2)

Guidance literature:

With trifluoroacetic acid; In dichloromethane; toluene; at 20 ℃; for 1h;

DOI:10.1007/s00726-008-0221-8

Reference yield: 96.0%

(S)-4-isobutyl-5-oxooxazolidine-3-carboxylic acid 9H-fluoren-9-ylmethyl ester → N-(9-fluorenylmethoxycarbonyl)-N-methyl-L-leucine (103478-62-2)

Guidance literature:

With triethylsilane; trifluoroacetic acid; In chloroform; at 20 ℃; for 31h;

DOI:10.1016/j.tet.2018.09.011

Reference yield: 88.0%

formaldehyd (50-00-0,30525-89-4,61233-19-0) + Fmoc-Leu-OH (35661-60-0) → N-(9-fluorenylmethoxycarbonyl)-N-methyl-L-leucine (103478-62-2)

Guidance literature:

formaldehyd; Fmoc-Leu-OH; With (1S)-10-camphorsulfonic acid; In toluene; at 160 ℃; for 3h; Dean-Stark;

With triethylsilane; trifluoroacetic acid; In dichloromethane; at 20 ℃;

DOI:10.1021/acs.jmedchem.1c00211

upstream raw materials:

Nα-(4-nitrobenzenesulfonyl)-L-leucine

diazomethane

(fluorenylmethoxy)carbonyl chloride

formaldehyd

Downstream raw materials:

N-<(9-fluorenylmethyl)oxy>carbonyl-N-methylleucylalanine benzyl ester

N-<(9-fluorenylmethyl)oxy>carbonyl-N-methylleucylvalyl-N-methylleucylalanine benzyl ester

Refernces

• 1、 Chatterjee, Jayanta,Ovadia, Oded,Zahn, Grit,Marinelli, Luciana,Hoffman, Amnon,Gilon, Chaim,Kessler, Horst. "Multiple N-methylation by a designed approach enhances receptor selectivity". . p. 5878 - 5881. Retrieved 2007.
• 2、 Bockus, Andrew T.,Lexa, Katrina W.,Pye, Cameron R.,Kalgutkar, Amit S.,Gardner, Jarret W.,Hund, Kathryn C.R.,Hewitt, William M.,Schwochert, Joshua A.,Glassey, Emerson,Price, David A.,Mathiowetz, Alan M.,Liras, Spiros,Jacobson, Matthew P.,Lokey, R. Scott. "Probing the Physicochemical Boundaries of Cell Permeability and Oral Bioavailability in Lipophilic Macrocycles Inspired by Natural Products". . p. 4581 - 4589. Retrieved 2015.
• 3、 Li, Daichun,Liao, Xiaojian,Xu, Shihai,Zhao, Bingxin,Zhong, Shenghui. "Synthesis of Marine Cyclopeptide Galaxamide Analogues as Potential Anticancer Agents". . . Retrieved 2022/03/02.