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

Base Information

• Chemical Name: (S)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)(methyl)amino)-3-phenylpropanoic acid
• CAS No.: 77128-73-5
• Molecular Formula: C25H23NO4
• Molecular Weight: 401.462
• Hs Code.: 2924 29 70
• European Community (EC) Number: 844-850-8
• Nikkaji Number: J2.281.974G
• Mol file: 77128-73-5.mol

Synonyms:77128-73-5;Fmoc-N-Me-Phe-OH;Fmoc-MePhe-OH;Fmoc-N-methyl-L-phenylalanine;(S)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)(methyl)amino)-3-phenylpropanoic acid;N-Fmoc-N-methyl-L-phenylalanine;Fmoc-N-Me-L-Phe-OH;L-Phenylalanine, N-[(9H-fluoren-9-ylmethoxy)carbonyl]-N-methyl-;(2S)-2-[9H-fluoren-9-ylmethoxycarbonyl(methyl)amino]-3-phenylpropanoic acid;MFCD00151938;N-alpha-(9-Fluorenylmethyloxycarbonyl)-N-alpha-methyl-L-phenylalanine;Fmoc-Nalpha-methyl-L-phenylalanine;N-[(9H-Fluoren-9-ylmethoxy)carbonyl]-N-methyl-L-phenylalanine;SCHEMBL120595;GBROUWPNYVBLFO-QHCPKHFHSA-N;ZB0880;AKOS015837150;AKOS015908459;CS-W011702;HY-W010986;AC-24162;AM808172;DS-13395;F1167;EN300-1692653;A850900;Fmoc-N-Me-Phe-OH, >=99.0% (sum of enantiomers, HPLC);N-(((9H-Fluoren-9-yl)methoxy)carbonyl)-N-methyl-L-phenylalanine;(2S)-2-({[(9H-fluoren-9-yl)methoxy]carbonyl}(methyl)amino)-3-phenylpropanoic acid;(S)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)(methyl)amino)-3-phenylpropanoicacid

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

Chemical Property:

• Appearance/Colour: white powder
• Melting Point: 132.0 to 136.0 °C
• Boiling Point: 595.4 °C at 760 mmHg
• PKA: 3.78±0.10(Predicted)
• Flash Point: 313.9 °C
• PSA: 66.84000
• Density: 1.26 g/cm³
• LogP: 4.56320
• Storage Temp.: 2-8°C
• Solubility.: Soluble in DMF. (0.3gram in 2ml)
• 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% ^*data from raw suppliers

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

Safty Information:

• Safety Statements: 22-24/25

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: N-Fmoc-N-methyl-L-phenylalanine is used in agrochemical, pharmaceutical and dyestuff field.

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

There total 14 articles about (S)-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: 99.0%

9H-fluoren-9-ylmethyl (S)-4-benzyl-5-oxo-1,3-oxazolidine-3-carboxylate (84000-03-3) → (2S)-N-fluorenylmethyloxycarbonyl-2-amino-N-methyl-3-phenylpropanoic acid (77128-73-5,1362858-91-0)

Guidance literature:

With triethylsilane; trifluoroacetic acid; In chloroform; at 20 ℃; for 47h;

DOI:10.1016/j.tet.2018.09.011

Reference yield: 91.0%

N-Methyl-L-phenylalanine (2566-30-5) + (fluorenylmethoxy)carbonyl chloride (28920-43-6) → (2S)-N-fluorenylmethyloxycarbonyl-2-amino-N-methyl-3-phenylpropanoic acid (77128-73-5,1362858-91-0)

Guidance literature:

With sodium carbonate; In 1,4-dioxane; a) ice-bath, 1 h, b) r.t., 3 h;

DOI:10.1021/jo00015a011

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

upstream raw materials:

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

N-Fmoc L-Phe

N-Methyl-L-phenylalanine

(fluorenylmethoxy)carbonyl chloride

Downstream raw materials:

H-Tyr-D-Orn[*]-Phe(NMe)-Asp[*]-NH₂

(S)-2-[(9H-Fluoren-9-ylmethoxycarbonyl)-methyl-amino]-3-phenyl-propionic acid 2,5-dioxo-pyrrolidin-1-yl ester

C₄₉H₇₄N₈O₁₃S

Refernces

• 1、 Mazuela, Javier,Antonsson, Thomas,Knerr, Laurent,Marsden, Stephen P.,Munday, Rachel H.,Johansson, Magnus J.. "Iridium-Catalyzed Asymmetric Hydrogenation of N-Alkyl α-Aryl Furan-Containing Imines: an Efficient Route to Unnatural N-Alkyl Arylalanines and Related Derivatives". supporting information. p. 578 - 584. Retrieved 2018/12/11.
• 2、 Bai, Xiaohui,Niu, Youhong,Zhu, Jingjing,Yang, An-Qi,Wu, Yan-Fen,Ye, Xin-Shan. "A new GLP-1 analogue with prolonged glucose-lowering activity in vivo via backbone-based modification at the N-terminus". . p. 1163 - 1170. Retrieved 2016/03/01.