(S)-2-Amino-3-(1,3,5,7-pentahydro-2,4-dioxo-cyclopenta[E]pyrimidin-1-YL) proionic acid

Base Information

• Chemical Name: (S)-2-Amino-3-(1,3,5,7-pentahydro-2,4-dioxo-cyclopenta[E]pyrimidin-1-YL) proionic acid
• CAS No.: 389888-02-2
• Molecular Formula: C₁₀H₁₃N₃O₄
• Molecular Weight: 239.231
• DSSTox Substance ID: DTXSID50349678
• Nikkaji Number: J1.679.221G
• Wikidata: Q12061559
• Metabolomics Workbench ID: 147771
• ChEMBL ID: CHEMBL337577
• Mol file: 389888-02-2.mol

Synonyms:389888-02-2;(S)-2-AMINO-3-(1,3,5,7-PENTAHYDRO-2,4-DIOXO-CYCLOPENTA[E]PYRIMIDIN-1-YL) PROIONIC ACID;(2S)-2-amino-3-(2,4-dioxo-6,7-dihydro-5H-cyclopenta[d]pyrimidin-1-yl)propanoic acid;CHEMBL337577;CPW;1syh;1syi;SCHEMBL16343833;DTXSID50349678;BDBM50107595;AKOS024456656;DB03240;NCGC00159527-01;PD007308;Q12061559;(S)-?-Amino-2,3,4,5,6,7-hexahydro-2,4-dioxo-1H-cyclopentapyrimidine-1-propanoic acid;(S)-1-(2-Amino-2-carboxyethyl)-6,7-dihydro-1H-cyclopenta[d]-pyrimidin-2,4(1H,3H)dione;(S)-alpha-Amino-2,3,4,5,6,7-hexahydro-2,4-dioxo-1H-cyclopentapyrimidine-1-propanoic acid;2-Amino-3-(2,4-dioxo-2,3,4,5,6,7-hexahydro-cyclopentapyrimidin-1-yl)-propionic acid;3-(2,4-dioxo-2,3,4,5,6,7-hexahydro-1H-cyclopenta[d]pyrimidin-1-yl)-L-alanine;(2S)-2-amino-3-{2,4-dioxo-1H,2H,3H,4H,5H,6H,7H-cyclopenta[d]pyrimidin-1-yl}propanoic acid;(S)-2-Amino-3-(2,4-dioxo-2,3,4,5,6,7-hexahydro-1H-cyclopenta[d]pyrimidin-1-yl)propanoic acid;(S)-2-Amino-3-(2,4-dioxo-2,3,4,5,6,7-hexahydro-1H-cyclopenta[d]pyrimidin-1-yl)propanoicacid

Chemical Property of (S)-2-Amino-3-(1,3,5,7-pentahydro-2,4-dioxo-cyclopenta[E]pyrimidin-1-YL) proionic acid

Chemical Property:

• PSA: 118.18000
• LogP: -0.86250
• Storage Temp.: Desiccate at -20°C
• Solubility.: Aqueous Acid (Slightly, Heated, Sonicated), DMSO (Slightly)
• XLogP3: -3.7
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 3
• Exact Mass: 239.09060590
• Heavy Atom Count: 17
• Complexity: 429

Purity/Quality:

98.5% ^*data from raw suppliers

(S)-CPW399 ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CC2=C(C1)N(C(=O)NC2=O)CC(C(=O)O)N
• Isomeric SMILES: C1CC2=C(C1)N(C(=O)NC2=O)C[C@@H](C(=O)O)N
• Uses: (S)-CPW 399 is a subtype-selective weakly desensitising AMPA agonist.

Technology Process of (S)-2-Amino-3-(1,3,5,7-pentahydro-2,4-dioxo-cyclopenta[E]pyrimidin-1-YL) proionic acid

There total 4 articles about (S)-2-Amino-3-(1,3,5,7-pentahydro-2,4-dioxo-cyclopenta[E]pyrimidin-1-YL) proionic 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:

1,5,6,7-tetrahydro-cyclopentapyrimidine-2,4-dione (5466-00-2) + (S)-3-(tert-butoxycarbonylamino)-oxetan-2-one (98541-64-1) → (S)-CPW 399 (389888-02-2)

Guidance literature:

1,5,6,7-tetrahydro-cyclopentapyrimidine-2,4-dione; With sodium hydride; In N,N-dimethyl-formamide; at 20 ℃;

(S)-3-(tert-butoxycarbonylamino)-oxetan-2-one; In N,N-dimethyl-formamide; Further stages.;

DOI:10.1021/jm015552m

Reference yield:

2-sulfanylidene-1,2,3,4,6,7-hexahydro-5H-cyclopenta[d]pyrimidin-4-one (35563-27-0) → (S)-CPW 399 (389888-02-2)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 82 percent / chloroacetic acid / methanol / 16 h / Heating

2.1: sodium hydride / dimethylformamide; various solvent(s) / 20 °C

2.2: dimethylformamide; various solvent(s)

With sodium hydride; chloroacetic acid; In methanol; N,N-dimethyl-formamide;

DOI:10.1021/jm015552m

Reference yield:

2-ethoxycarbonyl-1-cyclopentanone (611-10-9) → (S)-CPW 399 (389888-02-2)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 20 percent / 2.5 h / 180 °C

2.1: 82 percent / chloroacetic acid / methanol / 16 h / Heating

3.1: sodium hydride / dimethylformamide; various solvent(s) / 20 °C

3.2: dimethylformamide; various solvent(s)

With sodium hydride; chloroacetic acid; In methanol; N,N-dimethyl-formamide;

DOI:10.1021/jm015552m

upstream raw materials:

1,5,6,7-tetrahydro-cyclopentapyrimidine-2,4-dione

(S)-3-(tert-butoxycarbonylamino)-oxetan-2-one

2-sulfanylidene-1,2,3,4,6,7-hexahydro-5H-cyclopenta[d]pyrimidin-4-one

2-ethoxycarbonyl-1-cyclopentanone

Refernces