Fmoc-alpha-methylalanine

Base Information

• Chemical Name: Fmoc-alpha-methylalanine
• CAS No.: 94744-50-0
• Molecular Formula: C19H19NO4
• Molecular Weight: 325.364
• Hs Code.: 29242990
• European Community (EC) Number: 619-072-5
• DSSTox Substance ID: DTXSID90373235
• Nikkaji Number: J1.180.081E
• Wikidata: Q72478610
• Mol file: 94744-50-0.mol

Synonyms:Fmoc-Aib-OH;94744-50-0;Fmoc-alpha-methylalanine;Fmoc-2-Aminoisobutyric acid;2-(9H-fluoren-9-ylmethoxycarbonylamino)-2-methylpropanoic acid;2-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-2-methylpropanoic acid;2-(Fmoc-amino)isobutyric Acid;Alanine, N-[(9H-fluoren-9-ylmethoxy)carbonyl]-2-methyl-;MFCD00151913;EC 619-072-5;2-[(9H-Fluoren-9-ylmethoxy)carbonylamino]isobutyric Acid;N-a-Fmoc-a-aminoisobutyric acid, N-fmoc-c-a-methylalanine;N-Fmoc-2-methyl-DL-alanine;Fmoc-alpha-aminoisobutyric acid;2-({[(9H-FLUOREN-9-YL)METHOXY]CARBONYL}AMINO)-2-METHYLPROPANOIC ACID;Fmoc-alpha-methyl-alanine;N-Fmoc-alpha-methylalanine;Fmoc- alpha -Me-Ala-OH;SCHEMBL119779;DTXSID90373235;HOZZVEPRYYCBTO-UHFFFAOYSA-N;ZB0991;AKOS012614616;AC-6775;AM82455;CS-W009269;AS-18079;HY-79648;SY033784;Fmoc-Aib-OH 2-(Fmoc-amino)isobutyric acid;F0888;FT-0657236;EN300-81267;Fmoc-alpha-Me-Ala-OH, >=97.0% (HPLC);A22824;J-300334;Q-101780;N-(9H-Fluoren-9-ylmethoxycarbonyl)-2-methyl-L-alanine;Z1123720081;2-(((9H-fluoren-9-yl)methoxy)carbonylamino)-2-methylpropanoic acid;2-(9H-Fluoren-9-ylmethoxy-carbonylamino)-2-methyl-propionic acid;2-(9H-Fluoren-9-ylmethoxycarbonylamino)-2-methyl-propionic acid;FMOC-AIB-OH;N-FMOC-C-alpha-methylalanine;N-alpha-Fmoc-l-alpha-aminoisobutyric acid

Chemical Property of Fmoc-alpha-methylalanine

Chemical Property:

• Melting Point: 182-188 °C
• Refractive Index: 1.614
• Boiling Point: 544.3 °C at 760 mmHg
• PKA: 3.98±0.10(Predicted)
• Flash Point: 283 °C
• PSA: 75.63000
• Density: 1.256 g/cm³
• LogP: 3.77920
• Storage Temp.: 2-8°C
• Sensitive.: Moisture Sensitive
• XLogP3: 3.2
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 5
• Exact Mass: 325.13140809
• Heavy Atom Count: 24
• Complexity: 468

Purity/Quality:

≥98%, ^*data from raw suppliers

Fmoc-alpha-methylalanine ^*data from reagent suppliers

Safty Information:

• Safety Statements: 22-24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C(=O)O)NC(=O)OCC1C2=CC=CC=C2C3=CC=CC=C13
• Uses: L-Fmoc-Aminobutyric Acid, is an alanine derivative used in chemical synthesis and peptide chemistry. Fmoc-Aib-OH is used for studying receptor-ligand interactions using encoded amino acid scanning.

Technology Process of Fmoc-alpha-methylalanine

There total 5 articles about Fmoc-alpha-methylalanine 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: 97.0%

2-(9H-fluoren-9-ylmethoxycarbonylamino)-2-methyl-propionic acid tert-butyl ester → N-[(9H-fluoren-9-ylmethoxy)carbonyl]-α-aminoisobutyric acid (94744-50-0)

Guidance literature:

With ytterbium(III) triflate; In nitromethane; at 45 - 50 ℃; for 5h;

Reference yield: 83.0%

(fluorenylmethoxy)carbonyl chloride (28920-43-6) + 2-amino-2-methyl-propanoic acid hydrochloride (5938-34-1) → N-[(9H-fluoren-9-ylmethoxy)carbonyl]-α-aminoisobutyric acid (94744-50-0)

Guidance literature:

With water; sodium carbonate; In 1,4-dioxane; for 16h;

DOI:10.1002/(SICI)1521-3765(19980310)4:3<425::AID-CHEM425>3.0.CO;2-W

Reference yield: 70.0%

(fluorenylmethoxy)carbonyl chloride (28920-43-6) + 2-Aminoisobutyric acid (62-57-7) → N-[(9H-fluoren-9-ylmethoxy)carbonyl]-α-aminoisobutyric acid (94744-50-0)

Guidance literature:

With hydrogenchloride; zinc; In water; acetonitrile;

upstream raw materials:

(fluorenylmethoxy)carbonyl chloride

2-amino-2-methyl-propanoic acid hydrochloride

2-Aminoisobutyric acid

1,1,1,3',3',3'-hexafluoro-propanol

Downstream raw materials:

trans-2-Fluorenyl-methoxycarbonylamino-2-methyl-N-(4-nitroxycyclohexyl)-propionsaeureamid

Fmoc-Aib-SA

(S)-1-[2-(9H-Fluoren-9-ylmethoxycarbonylamino)-2-methyl-propionyl]-pyrrolidine-2-carboxylic acid tert-butyl ester

(S)-1-[2-({(2S,4R)-4-tert-Butoxy-1-[2-(9H-fluoren-9-ylmethoxycarbonylamino)-2-methyl-propionyl]-pyrrolidine-2-carbonyl}-amino)-2-methyl-propionyl]-pyrrolidine-2-carboxylic acid tert-butyl ester

Refernces

• 1、 -. "GLP-1 PRODRUGS". Page/Page column. . Retrieved 2015/02/25.
• 2、 Brown, Zachary Z.,Schafmeister, Christian E.. "Exploiting an inherent neighboring group effect of α-amino acids to synthesize extremely hindered dipeptides". supporting information; experimental part. p. 14382 - 14383. Retrieved 2009/02/08.