(R)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)(methyl)amino)-3-phenylpropanoic acid

Base Information

• Chemical Name: (R)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)(methyl)amino)-3-phenylpropanoic acid
• CAS No.: 138775-05-0
• Molecular Formula: C25H23NO4
• Molecular Weight: 401.462
• Hs Code.: 2924297099
• European Community (EC) Number: 874-502-0
• Nikkaji Number: J2.476.103G
• Mol file: 138775-05-0.mol

Synonyms:138775-05-0;Fmoc-D-Mephe-Oh;Fmoc-N-methyl-D-phenylalanine;(R)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)(methyl)amino)-3-phenylpropanoic acid;Fmoc-Nalpha-methyl-D-phenylalanine;Fmoc-N-Me-D-Phe-OH;D-Phenylalanine, N-[(9H-fluoren-9-ylmethoxy)carbonyl]-N-methyl-;(2R)-2-[9H-fluoren-9-ylmethoxycarbonyl(methyl)amino]-3-phenylpropanoic acid;N-[(9H-Fluoren-9-ylmethoxy)carbonyl]-N-methyl-D-phenylalanine;N-Fmoc-N-methyl-D-phenylalanine;MFCD00153392;Fmoc-NMe(D)Phe-OH;SCHEMBL120592;Fmoc-N-|A-methyl-D-Phenylalanine;AC2471;AKOS015837205;AM82188;AC-24161;DS-13642;HY-34470;PD195981;CS-0020043;Fmoc-N-Me-D-Phe-OH, >=98.0% (HPLC);EN300-1703203;(R)-2-(Fmoc-(methyl)amino)-3-phenylpropanoic acid;N-(((9H-Fluoren-9-yl)methoxy)carbonyl)-N-methyl-D-phenylalanine;N-alpha-(9-Fluorenylmethyloxycarbonyl)-N-alpha-methyl-D-phenylalanine;(2R)-2-({[(9H-fluoren-9-yl)methoxy]carbonyl}(methyl)amino)-3-phenylpropanoic acid

Chemical Property of (R)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)(methyl)amino)-3-phenylpropanoic acid

Chemical Property:

• Vapor Pressure: 5.02E-15mmHg at 25°C
• Refractive Index: 1.629
• Boiling Point: 595.439 °C at 760 mmHg
• PKA: 3.78±0.10(Predicted)
• Flash Point: 313.911 °C
• PSA: 66.84000
• Density: 1.261 g/cm³
• LogP: 4.56320
• Storage Temp.: 2-8°C
• XLogP3: 4.8
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 7
• Exact Mass: 401.16270821
• Heavy Atom Count: 30
• Complexity: 580

Purity/Quality:

98%min ^*data from raw suppliers

N-alpha-Fmoc-N-alpha-Methyl-D-phenylalanine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CN(C(CC1=CC=CC=C1)C(=O)O)C(=O)OCC2C3=CC=CC=C3C4=CC=CC=C24
• Isomeric SMILES: CN([C@H](CC1=CC=CC=C1)C(=O)O)C(=O)OCC2C3=CC=CC=C3C4=CC=CC=C24
• Uses: Fmoc-D-MePhe-OH is an intermediate used in the preparation of fluorinated analogs of pepstatin A and grassystatin A that functions as inhibitors of aspartic protease enzymes.

Technology Process of (R)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)(methyl)amino)-3-phenylpropanoic acid

There total 8 articles about (R)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)(methyl)amino)-3-phenylpropanoic 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: 76.0%

N-nosyl-D-phenylalanine (852852-85-8) + diazomethane (186581-53-3,908094-01-9,334-88-3) + (fluorenylmethoxy)carbonyl chloride (28920-43-6) → (2R)-2-(N-(((9H-fluoren-9-yl)methoxy)carbonyl)-N-methylamino)-3-phenyl-propionic acid (138775-05-0,1362858-91-0)

Guidance literature:

Multistep reaction.;

DOI:10.1021/jo070075m

Reference yield: 70.0%

9H-fluoren-9-ylmethyl (S)-4-benzyl-5-oxo-1,3-oxazolidine-3-carboxylate (84000-03-3) → N-Fmoc-N-methyl-L-phenylalanine (77128-73-5,138775-05-0,1362858-91-0)

Guidance literature:

With triethylsilane; trifluoroacetic acid; In chloroform; for 22h; Ambient temperature;

DOI:10.1021/jo00149a016

Reference yield:

N-methyl-D-phenylalanine (56564-52-4) → (2R)-2-(N-(((9H-fluoren-9-yl)methoxy)carbonyl)-N-methylamino)-3-phenyl-propionic acid (138775-05-0,1362858-91-0)

Guidance literature:

Multi-step reaction with 2 steps

1: acetonitrile / 0.5 h / 60 °C

2: acetonitrile / 1 h / 0 °C

In acetonitrile;

DOI:10.1021/acs.orglett.0c02984

upstream raw materials:

9H-fluoren-9-ylmethyl (S)-4-benzyl-5-oxo-1,3-oxazolidine-3-carboxylate

N-Fmoc L-Phe

N-nosyl-D-phenylalanine

diazomethane

Downstream raw materials:

NH₂-Phe-Me-D-Phe-D-Lys(2-Cl-Z)-Lys(Boc)-Leu-OH

NH-Me-D-Phe-D-Lys(2-Cl-Z)-Val-Lys(Boc)-Phe-OH

Refernces

• 1、 Cary, Douglas R.,Handa, Michiharu,Kobayashi, Yutaka,Kurasaki, Haruaki,Masuya, Keiichi,Matsuda, Ayumu,Matsumoto, Masatoshi,Morimoto, Koki,Nagaya, Akihiro,Nishizawa, Naoki,Taguri, Tomonori,Takeuchi, Hisayuki. "Isostearyl Mixed Anhydrides for the Preparation of N-Methylated Peptides Using C-Terminally Unprotected N-Methylamino Acids". supporting information. p. 8039 - 8043. Retrieved 2020/11/02.
• 2、 Di Gioia, Maria Luisa,Leggio, Antonella,Liguori, Angelo,Perri, Francesca. "Solid-phase synthesis of N-nosyl- and N-Fmoc-N-methyl-α-amino acids". . p. 3723 - 3728. Retrieved 2008/02/05.