2-(9H-fluoren-9-ylmethoxycarbonylamino)-4-methylpentanoic acid

Base Information

• Chemical Name: 2-(9H-fluoren-9-ylmethoxycarbonylamino)-4-methylpentanoic acid
• CAS No.: 126727-03-5
• Molecular Formula: C21H23NO4
• Molecular Weight: 353.418
• NSC Number: 334290
• DSSTox Substance ID: DTXSID00860520
• Wikidata: Q27077695
• Pharos Ligand ID: YKHJFC7YKWU1
• ChEMBL ID: CHEMBL294989
• Mol file: 126727-03-5.mol

Synonyms:126727-03-5;Fmoc-DL-leucine;DL-LEUCINE-D10-N-FMOC;2-(9H-fluoren-9-ylmethoxycarbonylamino)-4-methylpentanoic acid;CHEMBL294989;L-Leucine-d3-N-FMOC (methyl-d3);L-Leucine-15N, N-[(9H-fluoren-9-ylmethoxy)carbonyl]-;N-Fmoc-D-leucine;2-({[(9H-FLUOREN-9-YL)METHOXY]CARBONYL}AMINO)-4-METHYLPENTANOIC ACID;538372-74-6;MFCD00037133;MFCD00062957;NSC-334290;NSC334290;D03NZU;2-(9H-Fluoren-9-ylmethoxycarbonylamino)-4-methyl-pentanoic acid;GTPL2705;SCHEMBL1002861;CHEBI:91726;DTXSID00860520;HMS3266H19;BDBM50034787;AKOS001044199;AKOS017268980;AB01604;AB02467;NCGC00095919-01;NCGC00095919-02;SY035103;SY036884;FT-0626505;FT-0629919;EN300-17201;AB01273269-03;N-{[(9H-Fluoren-9-yl)methoxy]carbonyl}leucine;BRD-A47633927-001-01-8;Q27077695;Z56899084;2-(((9H-fluoren-9-yl)methoxy)carbonylamino)-4-methylpentanoic acid;N- (9-FLUORENYLMETHOXYCARBONYL)-L-LEUCINE (NPC-15199);2-({[(9H-FLUOREN-9-YL)METHOXY]CARBONYL}AMINO)-4-METHYLPENTANOICACID

Chemical Property of 2-(9H-fluoren-9-ylmethoxycarbonylamino)-4-methylpentanoic acid

Chemical Property:

• PSA: 75.63000
• LogP: 4.41530
• XLogP3: 4.4
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 7
• Exact Mass: 353.16270821
• Heavy Atom Count: 26
• Complexity: 484

Purity/Quality:

98.5% ^*data from raw suppliers

DL-Leucine-d10-N-FMOC ^*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)NC(=O)OCC1C2=CC=CC=C2C3=CC=CC=C13
• Uses: DL-Leucine-d10-N-FMOC is a useful isotopically labeled compound

Technology Process of 2-(9H-fluoren-9-ylmethoxycarbonylamino)-4-methylpentanoic acid

There total 13 articles about 2-(9H-fluoren-9-ylmethoxycarbonylamino)-4-methylpentanoic acid 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: 85.0%

(fluorenylmethoxy)carbonyl chloride (28920-43-6) + LEUCINE (328-39-2,21675-61-6,25248-98-0,70-45-1) → 2-(9H-Fluoren-9-ylmethoxycarbonylamino)-4-methyl-pentanoic acid (126727-03-5)

Guidance literature:

With sodium carbonate; In 1,4-dioxane; water; at 20 ℃;

DOI:10.1021/acs.jmedchem.9b02119

Reference yield: 82.0%

C22H23N3O3 (244227-56-3) → N-(9-fluorenylmethoxycarbonyl)-D-leucine (35661-60-0,126727-03-5,114360-54-2)

Guidance literature:

With 4-methyl-morpholine; silver trifluoroacetate; In tetrahydrofuran; water; at 0 - 20 ℃;

Reference yield:

(fluorenylmethoxy)carbonyl chloride (28920-43-6) + (R)-2-Amino-4-methyl-pentanoic acid ((1S,2S)-2-hydroxy-1-methyl-2-phenyl-ethyl)-methyl-amide (170642-24-7) → pseudoephedrine (90-82-4,7009-81-6,90-83-5,6912-63-6) + N-(9-fluorenylmethoxycarbonyl)-D-leucine (35661-60-0,126727-03-5,114360-54-2)

Guidance literature:

With sodium hydroxide; sodium hydrogencarbonate; Yield given. Multistep reaction; 1.) reflux, 2.) 1.5 h;

DOI:10.1021/ja00137a034

upstream raw materials:

(fluorenylmethoxy)carbonyl chloride

LEUCINE

(R)-2-Amino-4-methyl-pentanoic acid ((1S,2S)-2-hydroxy-1-methyl-2-phenyl-ethyl)-methyl-amide

(R)-leucine

Downstream raw materials:

2-tert-butoxycarbonylamino-4-methyl-pentanoic acid 5-{2-[2-(9H-fluoren-9-ylmethoxycarbonylamino)-4-methyl-pentanoylamino]-phenyl}-5-oxo-pentyl ester

Fmoc-Leu-OH

N-(9-fluorenylmethoxycarbonyl)-D-leucine

human C-type natriuretic peptide 22

Refernces

• 1、 -. "Kras inhibitory cyclic peptide compound". Paragraph 0682; 0821; 0824. . Retrieved 2021/06/03.
• 2、 Islam, Md. Fokhrul,Adhikari, Suraj,Paik, Man-Jeong,Lee, Wonjae. "Determination of Chemical and Enantiomeric Purity of α-Amino Acids and their Methyl Esters as N-Fluorenylmethoxycarbonyl Derivatives Using Amylose-derived Chiral Stationary Phases". . p. 332 - 338. Retrieved 2019/04/13.