alpha-Amino-2'-chloro-5-(phosphonomethyl)(1,1'-biphenyl)-3-propanoic acid

Base Information

• Chemical Name: alpha-Amino-2'-chloro-5-(phosphonomethyl)(1,1'-biphenyl)-3-propanoic acid
• CAS No.: 174575-17-8
• Molecular Formula: C₁₆H₁₇ClNO₅P
• Molecular Weight: 369.741
• European Community (EC) Number: 803-293-0
• DSSTox Substance ID: DTXSID301146157
• Nikkaji Number: J695.466I
• ChEMBL ID: CHEMBL1331280
• Mol file: 174575-17-8.mol

Synonyms:alpha-amino-2'-chloro-5-(phosphonomethyl)(1,1'-biphenyl)-3-propanoic acid;SDZ 220-581;SDZ 220-581, (R)-isomer;SDZ-220-581

Chemical Property of alpha-Amino-2'-chloro-5-(phosphonomethyl)(1,1'-biphenyl)-3-propanoic acid

Chemical Property:

• Vapor Pressure: 6.75E-16mmHg at 25°C
• Boiling Point: 613.3°C at 760 mmHg
• PKA: 1.63±0.10(Predicted)
• Flash Point: 324.7°C
• PSA: 130.66000
• Density: 1.478
• LogP: 3.33940
• Storage Temp.: Store at RT
• XLogP3: -1.2
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 6
• Exact Mass: 369.0532873
• Heavy Atom Count: 24
• Complexity: 485

Purity/Quality:

97% ^*data from raw suppliers

SDZ220-581 ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C(=C1)C2=CC(=CC(=C2)CP(=O)(O)O)CC(C(=O)O)N)Cl
• Isomeric SMILES: C1=CC=C(C(=C1)C2=CC(=CC(=C2)CP(=O)(O)O)C[C@@H](C(=O)O)N)Cl
• Uses: SDZ 220-581 is a competitive NMDA receptor antagonist.

Technology Process of alpha-Amino-2'-chloro-5-(phosphonomethyl)(1,1'-biphenyl)-3-propanoic acid

There total 6 articles about alpha-Amino-2'-chloro-5-(phosphonomethyl)(1,1'-biphenyl)-3-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:

C28H44ClN2O4PSi2 → SDZ 220-581 (174575-17-8)

Guidance literature:

With Dowex 50 W; sulfuric acid; In xylene; Yield given; 1.) 70 deg C, 4 h; 2.) reflux, 144 h;

DOI:10.1002/hlca.19950780810

Reference yield:

1-bromo-3,5-bis(bromomethyl)benzene (51760-23-7) → SDZ 220-581 (174575-17-8)

Guidance literature:

Multi-step reaction with 5 steps

1: 47 percent / xylene / 2 h / Heating

2: 69 percent / (i-Pr)2NH, 1.6M BuLi / tetrahydrofuran; hexane / 1.67 h / -70 °C

3: 81 percent / 2M aq. Na₂CO₃, PPh₃, Pd(OAc)2 / ethanol; toluene / 6 h / 100 °C / ultrasonic bath

4: acetonitrile / 24 h / Ambient temperature

5: 1.) 0.375M aq. H₂SO₄; 2.) Dowex 50 W / xylene / 1.) 70 deg C, 4 h; 2.) reflux, 144 h

With palladium diacetate; n-butyllithium; Dowex 50 W; sulfuric acid; sodium carbonate; diisopropylamine; triphenylphosphine; In tetrahydrofuran; ethanol; hexane; toluene; acetonitrile; xylene;

DOI:10.1002/hlca.19950780810

Reference yield:

5-bromo-1,3-dihydroxymethylbenzene (51760-22-6) → SDZ 220-581 (174575-17-8)

Guidance literature:

Multi-step reaction with 6 steps

1: PPh₃ / toluene / 2 h / 80 °C

2: 47 percent / xylene / 2 h / Heating

3: 69 percent / (i-Pr)2NH, 1.6M BuLi / tetrahydrofuran; hexane / 1.67 h / -70 °C

4: 81 percent / 2M aq. Na₂CO₃, PPh₃, Pd(OAc)2 / ethanol; toluene / 6 h / 100 °C / ultrasonic bath

5: acetonitrile / 24 h / Ambient temperature

6: 1.) 0.375M aq. H₂SO₄; 2.) Dowex 50 W / xylene / 1.) 70 deg C, 4 h; 2.) reflux, 144 h

With palladium diacetate; n-butyllithium; Dowex 50 W; sulfuric acid; sodium carbonate; diisopropylamine; triphenylphosphine; In tetrahydrofuran; ethanol; hexane; toluene; acetonitrile; xylene;

DOI:10.1002/hlca.19950780810

upstream raw materials:

1-bromo-3,5-bis(bromomethyl)benzene

5-bromo-1,3-dihydroxymethylbenzene

diethyl <<3-bromo-5-(bromomethyl)phenyl>methyl>phosphonate

1,1-dimethylethyl (2S,5S)-5-<<3-bromo-5-<(diethoxyphosphoryl)methyl>phenyl>methyl>-2-(1,1-dimethylethyl)-3-methyl-4-oxoimidazolidine-1-carboxylate