(S)-2-Amino-3-(4-fluorophenyl)-2-methylpropanoic acid

Base Information

• Chemical Name: (S)-2-Amino-3-(4-fluorophenyl)-2-methylpropanoic acid
• CAS No.: 130855-57-1
• Molecular Formula: C10H12FNO2
• Molecular Weight: 197.209
• Hs Code.: 2922499990
• DSSTox Substance ID: DTXSID60469114
• Mol file: 130855-57-1.mol

Synonyms:130855-57-1;(S)-2-Amino-3-(4-fluorophenyl)-2-methylpropanoic acid;alpha-methyl-L-4-Fluorophenylalanine;alpha-methyl-L-4-Fluorophe;(2S)-2-AMINO-3-(4-FLUOROPHENYL)-2-METHYLPROPANOIC ACID;H-4-fluoro-alpha-Me-Phe-OH;4-Fluoro-alpha-methyl-L-phenylalanine;L-Phenylalanine, 4-fluoro-alpha-methyl-;H-4-fluoro--Me-Phe-OH;SCHEMBL1817058;DTXSID60469114;4-Fluoro-a-methyl-L-phenylalanine;MFCD08061612;AKOS016843481;AB43348;PS-12887;CS-0444272;A897969;(R)-alpha-Methyl-4-fluorophenylalanine, (R)-2-Amino-2-methyl-3-(4'-fluorophenyl)propanoic acid (H-D-aMePhe(4-F)-OH)

Chemical Property of (S)-2-Amino-3-(4-fluorophenyl)-2-methylpropanoic acid

Chemical Property:

• PSA: 63.32000
• LogP: 1.87050
• Storage Temp.: 2-8°C
• XLogP3: -1.1
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 197.08520679
• Heavy Atom Count: 14
• Complexity: 214

Purity/Quality:

97% ^*data from raw suppliers

4-Fluoro-α-methyl-L-phenylalanine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(CC1=CC=C(C=C1)F)(C(=O)O)N
• Isomeric SMILES: C[C@](CC1=CC=C(C=C1)F)(C(=O)O)N
• Uses: 4-Fluoro-α-methyl-L-phenylalanine is used in the discovery of series of zwitterionic CCR3 antagonists, AZ12436092.

Technology Process of (S)-2-Amino-3-(4-fluorophenyl)-2-methylpropanoic acid

There total 8 articles about (S)-2-Amino-3-(4-fluorophenyl)-2-methylpropanoic 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%

C35H32FN3O3(2-)*Ni(2+) → (2S)-2-amino-3-(4-fluorophenyl)-2-methylpropanoic acid (130855-57-1,422568-68-1)

Guidance literature:

With hydrogenchloride; In methanol; for 0.166667h; Heating;

DOI:10.1055/s-1993-25812

Reference yield: 78.0%

2-Amino-3-(4-fluoro-phenyl)-2-methyl-propionic acid methyl ester → (2S)-2-amino-3-(4-fluorophenyl)-2-methylpropanoic acid (130855-57-1,422568-68-1) + (R)-2-Amino-3-(4-fluoro-phenyl)-2-methyl-propionic acid methyl ester

Guidance literature:

With α-chymotrypsin; In water; at 37 ℃; for 35h; pH=5.0;

DOI:10.1016/S0040-4039(00)87608-X

Reference yield:

isopropyl 2-[(E)-1-phenylmethylideneamino]propanoate (126402-81-1) + 1-chloromethyl-4-fluorobenzene (352-11-4) → (2S)-2-amino-3-(4-fluorophenyl)-2-methylpropanoic acid (130855-57-1,422568-68-1) + (R)-α-methyl-para-fluorophenylalanine (422568-68-1)

Guidance literature:

isopropyl 2-[(E)-1-phenylmethylideneamino]propanoate; 1-chloromethyl-4-fluorobenzene; With sodium hydroxide; (R,R)-N,N'-bis(salicylidene)-1,2-cyclohexanediaminocopper(II); In toluene; at 20 ℃; for 12h; phase transfer catalysis;

With hydrogenchloride;

DOI:10.1016/S0040-4039(99)01214-9

upstream raw materials:

L-alanin

1-chloromethyl-4-fluorobenzene

isopropyl 2-[(E)-1-phenylmethylideneamino]propanoate

4-Fluorobenzyl bromide

Downstream raw materials:

3-(S)-(4-fluoro-phenyl)-2-methyl-2-pyrrol-1-yl-propionic acid

N-{3-[5-(S)-(4-fluoro-benzyl)-8-hydroxy-5-methyl-6-oxo-5,6-dihydro-indolizin-7-yl]-1,1-dioxo-1,4-dihydro-1λ6-benzo[1,2,4]thiadiazin-7-yl}-methanesulfonamide

5-(S)-(4-fluoro-benzyl)-8-hydroxy-5-methyl-6-oxo-5,6-dihydro-indolizine-7-carboxylic acid ethyl ester