2-Amino-2-(4-phosphonophenyl)propanoic acid

Base Information

• Chemical Name: 2-Amino-2-(4-phosphonophenyl)propanoic acid
• CAS No.: 169209-65-8
• Molecular Formula: C₉H₁₂NO₅P
• Molecular Weight: 245.172
• DSSTox Substance ID: DTXSID80398316
• Nikkaji Number: J680.590F
• Wikidata: Q27087727
• Pharos Ligand ID: BGGMSJGRSFGS
• ChEMBL ID: CHEMBL86508
• Mol file: 169209-65-8.mol

Synonyms:MPPG;169209-65-8;2-amino-2-(4-phosphonophenyl)propanoic acid;(RS)-alpha-methyl-4-phosphonophenylglycine;CHEMBL86508;Benzeneacetic acid, alpha-amino-alpha-methyl-4-phosphono-;D0D2GL;GTPL1415;SCHEMBL12648709;DTXSID80398316;MPPG, >=97% (NMR), solid;BDBM50089910;AKOS024458668;(RS)-?-Methyl-4-phosphonophenylglycine;NCGC00024826-02;HY-101241;FT-0773250;2-Amino-2-(4-phosphono-phenyl)-propionic acid;L000410;SR-01000597457;J-010517;SR-01000597457-1;Q27087727;2-Amino-2-(4-phosphono-phenyl)-propionic acid(RS-MPPG)

Chemical Property of 2-Amino-2-(4-phosphonophenyl)propanoic acid

Chemical Property:

• Boiling Point: 507.9±60.0 °C(Predicted)
• PKA: 1?+-.0.10(Predicted)
• PSA: 130.66000
• Density: 1.54±0.1 g/cm3(Predicted)
• LogP: 0.44840
• Storage Temp.: Store at RT
• Solubility.: DMSO:
• XLogP3: -3.5
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 3
• Exact Mass: 245.04530948
• Heavy Atom Count: 16
• Complexity: 320

Purity/Quality:

98%min ^*data from raw suppliers

MPPG ^*data from reagent suppliers

Safty Information:

• Safety Statements: 22-24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C1=CC=C(C=C1)P(=O)(O)O)(C(=O)O)N
• Uses: MPPG is a potent antagonist of L-AP4-induced effects.

Technology Process of 2-Amino-2-(4-phosphonophenyl)propanoic acid

There total 14 articles about 2-Amino-2-(4-phosphonophenyl)propanoic 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: 78.0%

[4-((2R,4S)-3-Benzoyl-2-tert-butyl-1,4-dimethyl-5-oxo-imidazolidin-4-yl)-phenyl]-phosphonic acid diethyl ester (201608-22-2) → MPPG (169209-65-8,201608-25-5)

Guidance literature:

With hydrogenchloride; at 160 ℃; for 24h;

DOI:10.1039/a704704e

Reference yield:

(S)-2-[Benzyloxycarbonyl-((R)-2-hydroxy-1-phenyl-ethyl)-amino]-2-[4-(diethoxy-phosphoryl)-phenyl]-propionic acid methyl ester (220024-55-5) → MPPG (169209-65-8,201608-25-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 88 percent / H₂ / Pd/C / methanol / 760 Torr

2: 1.) Pb(OAc)4, 2.) 6N HCl, 3.) propylene oxide / 1.) CH₂Cl₂, MeOH, 0 deg C, 30 min, 2.) reflux, 24 h, 3.) EtOH, reflux, 15 min

With lead(IV) acetate; hydrogenchloride; hydrogen; methyloxirane; palladium on activated charcoal; In methanol;

DOI:10.1021/jo981297a

Reference yield:

N-[(R)-(2-hydroxy-1-phenylethyl)]-(S/R)-2-amino-2-methyl-(4'-bromophenyl)acetic acid methyl ester → MPPG (169209-65-8,201608-25-5)

Guidance literature:

Multi-step reaction with 4 steps

1: 58 percent / DMAP, Et₃N / tetrahydrofuran / 12 h / Ambient temperature

2: 86 percent / Et₃N / Pd(PPh₃)4 / 4 h / 100 °C

3: 88 percent / H₂ / Pd/C / methanol / 760 Torr

4: 1.) Pb(OAc)4, 2.) 6N HCl, 3.) propylene oxide / 1.) CH₂Cl₂, MeOH, 0 deg C, 30 min, 2.) reflux, 24 h, 3.) EtOH, reflux, 15 min

With lead(IV) acetate; hydrogenchloride; dmap; hydrogen; triethylamine; methyloxirane; palladium on activated charcoal; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; methanol;

DOI:10.1021/jo981297a

upstream raw materials:

[4-((2R,4S)-3-Benzoyl-2-tert-butyl-1,4-dimethyl-5-oxo-imidazolidin-4-yl)-phenyl]-phosphonic acid diethyl ester

N-[(R)-(2-hydroxy-1-phenylethyl)]-(S)-2-amino-2-methyl-(4'-diethylphosphonophenyl)acetic acid methyl ester

(S)-2-[Benzyloxycarbonyl-((R)-2-hydroxy-1-phenyl-ethyl)-amino]-2-[4-(diethoxy-phosphoryl)-phenyl]-propionic acid methyl ester

(S)-2-[Benzyloxycarbonyl-((R)-2-hydroxy-1-phenyl-ethyl)-amino]-2-(4-bromo-phenyl)-propionic acid methyl ester

Refernces

• 1、 Ma, Dawei,Tian, Hongqi. "Stereoselective synthesis of (S)-MPPG, (S)-MTPG and (S)-(+)-αM4CPG from (R)-4-hydroxyphenylglycine". . p. 3493 - 3496. Retrieved 2007/10/03.