(S)-3-((S)-5-Oxopyrrolidine-2-carbonyl)thiazolidine-4-carboxylic acid

Base Information

• Chemical Name: (S)-3-((S)-5-Oxopyrrolidine-2-carbonyl)thiazolidine-4-carboxylic acid
• CAS No.: 162148-16-5
• Molecular Formula: C₉H₁₂N₂O₄S
• Molecular Weight: 244.271
• UNII: P967H7R7VS
• Nikkaji Number: J531.561A
• Mol file: 162148-16-5.mol

Synonyms:162148-16-5;(S)-3-((S)-5-Oxopyrrolidine-2-carbonyl)thiazolidine-4-carboxylic acid;(4S)-3-[(2S)-5-OXOPYRROLIDINE-2-CARBONYL]-1,3-THIAZOLIDINE-4-CARBOXYLIC ACID;4S-Pidotimod;Pidotimod,(S);Pidotimod, (4S,2S)-;3-L-Pyroglutamyl-(S)-thiazolidine-4-carboxylic acid;P967H7R7VS;WS-01016;D86251;3-L-pyroglutamyl-D-thiazolidine-4-carboxylic acid;(S)-3-((S)-5-Oxopyrrolidine-2-carbonyl)thiazolidine-4-carboxylicacid;4-Thiazolidinecarboxylic acid, 3-[(5-oxo-2-pyrrolidinyl)carbonyl]-, [S-(R*,R*)]-

Chemical Property of (S)-3-((S)-5-Oxopyrrolidine-2-carbonyl)thiazolidine-4-carboxylic acid

Chemical Property:

• XLogP3: -0.7
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 2
• Exact Mass: 244.05177804
• Heavy Atom Count: 16
• Complexity: 346

Purity/Quality:

97% ^*data from raw suppliers

4S-Pidotimod ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: C1CC(=O)NC1C(=O)N2CSCC2C(=O)O
• Isomeric SMILES: C1CC(=O)N[C@@H]1C(=O)N2CSC[C@@H]2C(=O)O
• Uses: 4S-Pidotimod is a Pidotimod enantiomer and impurity with pharmacological properties.

Technology Process of (S)-3-((S)-5-Oxopyrrolidine-2-carbonyl)thiazolidine-4-carboxylic acid

There total 12 articles about (S)-3-((S)-5-Oxopyrrolidine-2-carbonyl)thiazolidine-4-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: 80.0%

ethyl-(R)-3-<(S)-(5-oxo-2-pyrrolidinyl)carbonyl>-thiazolidine-4-carboxylate (135124-63-9) → pidotimod (121808-62-6,162148-17-6,117241-40-4,162148-16-5)

Guidance literature:

With sodium hydroxide; for 1h;

Reference yield: 76.0%

pentachlorophenyl ester of L-pyroglutamic acid (28990-85-4) + L-thioproline (34592-47-7,2756-91-4,6070-92-4,60731-25-1) → pidotimod (121808-62-6,162148-17-6,117241-40-4,162148-16-5)

Guidance literature:

With triethylamine; In N,N-dimethyl-formamide; for 24h; Ambient temperature;

Reference yield:

L-Pyroglutamic acid (98-79-3) → pidotimod (121808-62-6,162148-17-6,117241-40-4,162148-16-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 78 percent / dicyclohexylcarbodiimide / CH₂Cl₂ / 1.) 0 deg C, 1 h; 2.) r.t., 4 h

2: 80 percent / 1 N NaOH / 1 h

With sodium hydroxide; dicyclohexyl-carbodiimide; In dichloromethane;

upstream raw materials:

ethyl-(R)-3-<(S)-(5-oxo-2-pyrrolidinyl)carbonyl>-thiazolidine-4-carboxylate

pentachlorophenyl ester of L-pyroglutamic acid

L-thioproline

L-Pyroglutamic acid