4-(Phosphonomethyl)piperazine-2-carboxylic acid

Base Information

• Chemical Name: 4-(Phosphonomethyl)piperazine-2-carboxylic acid
• CAS No.: 113919-36-1
• Molecular Formula: C6H13 N2 O5 P
• Molecular Weight: 224.153
• ChEMBL ID: CHEMBL29244
• DSSTox Substance ID: DTXSID30590848
• Nikkaji Number: J350.761K
• Mol file: 113919-36-1.mol

Synonyms:113919-36-1;PMPA (NMDA antagonist);4-(PHOSPHONOMETHYL)PIPERAZINE-2-CARBOXYLIC ACID;2-Piperazinecarboxylic acid, 4-(phosphonomethyl)-;Pmpa(nmda antagonist);CHEMBL29244;SCHEMBL1999794;DTXSID30590848;AKOS024457022;NCGC00159547-01;PD079296;HY-107698;J-003041

Chemical Property of 4-(Phosphonomethyl)piperazine-2-carboxylic acid

Chemical Property:

• PSA: 119.91000
• LogP: -1.25330
• Storage Temp.: Store at +4°C
• XLogP3: -7.1
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 3
• Exact Mass: 224.05620852
• Heavy Atom Count: 14
• Complexity: 265

Purity/Quality:

99% ^*data from raw suppliers

PMPA ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CN(CC(N1)C(=O)O)CP(=O)(O)O
• Uses: PMPA (NMDA antagonist) is a selective competitive antagonist at the NMDA receptor.

Technology Process of 4-(Phosphonomethyl)piperazine-2-carboxylic acid

There total 2 articles about 4-(Phosphonomethyl)piperazine-2-carboxylic 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: 86.0%

4-(Diethoxy-phosphorylmethyl)-piperazine-1,2-dicarboxylic acid 1-benzyl ester 2-methyl ester → 4-Phosphonomethyl-piperazine-2-carboxylic acid (113919-36-1)

Guidance literature:

With hydrogenchloride; 1.) reflux, 24 h, 2.) 25 deg C, 3.5 d;

DOI:10.1021/jm00172a037

Reference yield:

2-methyl 1-phenylmethyl 1,2-piperazinedicarboxilate, trifluoroacetate (126937-44-8) → 4-Phosphonomethyl-piperazine-2-carboxylic acid (113919-36-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 41 percent / K₂CO₃ / acetonitrile / 1.) reflux, 4 h, 2.) 25 deg C, 2.5 d

2: 86 percent / 6 M aq. HCl / 1.) reflux, 24 h, 2.) 25 deg C, 3.5 d

With hydrogenchloride; potassium carbonate; In acetonitrile;

DOI:10.1021/jm00172a037

upstream raw materials:

2-methyl 1-phenylmethyl 1,2-piperazinedicarboxilate, trifluoroacetate