(2r,4r)-2-[(4r)-2-(2-Hydroxyphenyl)-4,5-Dihydro-1,3-Thiazol-4-Yl]-3-Methyl-1,3-Thiazolidine-4-Carboxylic Acid

Base Information

• Chemical Name: (2r,4r)-2-[(4r)-2-(2-Hydroxyphenyl)-4,5-Dihydro-1,3-Thiazol-4-Yl]-3-Methyl-1,3-Thiazolidine-4-Carboxylic Acid
• CAS No.: 69772-54-9
• Deprecated CAS: 164104-31-8
• Molecular Formula: C₁₄H₁₆N₂O₃S₂
• Molecular Weight: 324.425
• DSSTox Substance ID: DTXSID601318690
• Nikkaji Number: J653.624G
• Wikidata: Q27135674
• Metabolomics Workbench ID: 64967
• ChEMBL ID: CHEMBL3099904
• Mol file: 69772-54-9.mol

Synonyms:pyochelin

Chemical Property of (2r,4r)-2-[(4r)-2-(2-Hydroxyphenyl)-4,5-Dihydro-1,3-Thiazol-4-Yl]-3-Methyl-1,3-Thiazolidine-4-Carboxylic Acid

Chemical Property:

• Vapor Pressure: 1.29E-15mmHg at 25°C
• Boiling Point: 593.4°C at 760 mmHg
• Flash Point: 312.7°C
• PSA: 123.73000
• Density: 1.462g/cm³
• LogP: 1.08560
• XLogP3: -0.3
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 3
• Exact Mass: 324.06023472
• Heavy Atom Count: 21
• Complexity: 446

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CN1C(CSC1C2CSC(=N2)C3=CC=CC=C3O)C(=O)O
• Isomeric SMILES: CN1[C@@H](CS[C@@H]1[C@H]2CSC(=N2)C3=CC=CC=C3O)C(=O)O
• Uses: Pyochelin is an iron-chelating growth promoter for Pseudomonas aeruginosa.

Technology Process of (2r,4r)-2-[(4r)-2-(2-Hydroxyphenyl)-4,5-Dihydro-1,3-Thiazol-4-Yl]-3-Methyl-1,3-Thiazolidine-4-Carboxylic Acid

There total 54 articles about (2r,4r)-2-[(4r)-2-(2-Hydroxyphenyl)-4,5-Dihydro-1,3-Thiazol-4-Yl]-3-Methyl-1,3-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: 70.0%

(R)-N-methylcysteine hydrochloride (14344-46-8,403804-61-5) + 2'-(2-hydroxyphenyl)-2'-thiazoline-4'-carboxaldehyde (163526-41-8) → pyochelin (338985-68-5,69772-54-9)

Guidance literature:

With potassium acetate; In ethanol; water; for 24h;

DOI:10.1016/S0040-4020(99)00946-1

Reference yield:

(R)-N-methylcysteine hydrochloride (14344-46-8,403804-61-5) + 2-(2-Hydroxyphenyl)-2-thiazoline-4-carboxaldehyde (118446-23-4) → Neopyochelin I (69772-54-9) + Pyochelin II (69772-54-9) + (4'S,2''R,4''R)-2'-(2-hydroxyphenyl)-3''-methyl-2'',3'',4'',4',5'-hexahydro-[2,4']-bisthiazolyl-4''-carboxylic acid (69772-54-9) + (4'R,2''R,4''R)-2'-(2-hydroxyphenyl)-3''-methyl-2'',3'',4'',4',5'-hexahydro-[2,4']-bisthiazolyl-4''-carboxylic acid (69772-54-9)

Guidance literature:

With potassium acetate; In ethanol; at 25 ℃; Yield given. Yields of byproduct given;

DOI:10.1021/jo00114a029

Reference yield:

(R)-N-methylcysteine hydrochloride (14344-46-8,403804-61-5) + 2-(2-Hydroxyphenyl)-2-thiazoline-4-carboxaldehyde (118446-23-4) → Neopyochelin I (69772-54-9) + Pyochelin II (69772-54-9) + (4'S,2''R,4''R)-2'-(2-hydroxyphenyl)-3''-methyl-2'',3'',4'',4',5'-hexahydro-[2,4']-bisthiazolyl-4''-carboxylic acid (69772-54-9) + (4'R,2''R,4''R)-2'-(2-hydroxyphenyl)-3''-methyl-2'',3'',4'',4',5'-hexahydro-[2,4']-bisthiazolyl-4''-carboxylic acid (69772-54-9)

Guidance literature:

With potassium acetate; In ethanol; at 25 ℃; Yield given. Yields of byproduct given;

DOI:10.1021/jo00114a029

upstream raw materials:

(R)-N-methylcysteine hydrochloride

2-(2-Hydroxyphenyl)-2-thiazoline-4-carboxaldehyde

N-methyl-L-cysteine

2'-(2-hydroxyphenyl)-2'-thiazoline-4'-carboxaldehyde