methyl (4R)-2-methyl-4,5-dihydro-1,3-thiazole-4-carboxylate

Base Information

• Chemical Name: methyl (4R)-2-methyl-4,5-dihydro-1,3-thiazole-4-carboxylate
• CAS No.: 2519-89-3
• Molecular Formula: C₆H₉NO₂S
• Molecular Weight: 159.209
• Nikkaji Number: J192.006E
• Mol file: 2519-89-3.mol

Synonyms:NS00045893

Chemical Property of methyl (4R)-2-methyl-4,5-dihydro-1,3-thiazole-4-carboxylate

Chemical Property:

• Vapor Pressure: 0.139mmHg at 25°C
• Melting Point: 22 - 24 °C
• Boiling Point: 216.6°C at 760 mmHg
• Flash Point: 84.8°C
• PSA: 63.96000
• Density: 1.3g/cm³
• LogP: 0.12880
• XLogP3: 0.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 2
• Exact Mass: 159.03539970
• Heavy Atom Count: 10
• Complexity: 179

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=NC(CS1)C(=O)OC
• Isomeric SMILES: CC1=N[C@@H](CS1)C(=O)OC

Technology Process of methyl (4R)-2-methyl-4,5-dihydro-1,3-thiazole-4-carboxylate

There total 12 articles about methyl (4R)-2-methyl-4,5-dihydro-1,3-thiazole-4-carboxylate 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: 85.0%

C8H12N6O4S2 + acetyl chloride (75-36-5) → methyl 2-methyl-4,5-dihydrothiazole-4-carboxylate (6436-58-4,15263-39-5,45789-42-2,2519-89-3)

Guidance literature:

acetyl chloride; With dmap; phenol; In chloroform; for 0.5h; Cooling with ice;

C₈H₁₂N₆O₄S₂; With triphenylphosphine; In chloroform; Reflux;

Reference yield: 73.0%

dimethyl (2R,2'R)-3,3'-disulfanediylbis(2-azidopropanoate) (1393377-75-7) + acetic acid (64-19-7,77671-22-8) → (4R)-2-methyl-4,5-dihydrothiazole-4-carboxylic acid methyl ester (2519-89-3,6436-58-4,15263-39-5,45789-42-2)

Guidance literature:

acetic acid; With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; In dichloromethane; at 20 ℃; for 0.25h;

dimethyl (2R,2'R)-3,3'-disulfanediylbis(2-azidopropanoate); With tributylphosphine; In dichloromethane; at 20 ℃; for 1h; Darkness;

With triphenylphosphine; In dichloromethane; for 5h; Reflux;

DOI:10.1021/jo301030k

Reference yield: 71.0%

C6H11NO3S (1084772-05-3) → (4R)-2-methyl-4,5-dihydrothiazole-4-carboxylic acid methyl ester (2519-89-3,6436-58-4,15263-39-5,45789-42-2)

Guidance literature:

With methanesulfonyl chloride; triethylamine; In dichloromethane; at 0 - 20 ℃; Inert atmosphere;

DOI:10.1016/j.tetlet.2008.09.014

upstream raw materials:

L-Cysteine methyl ester

O-ethyl acetimidate

ethyl acetimidate hydrochloride

cysteine methyl ester hydrochloride

Downstream raw materials:

l-cysteine hydrochloride

methyl 2-methyl-1,3-thiazole-4-carboxylate

Refernces

• 1、 Fang, Xinxin,Zhang, Kaifan,Yao, Hequan,Huang, Yue. "Cu(i)-Catalyzed oxidative homo-coupling of thiazoline-4-carboxylates: Synthesis of 4,4′-bithiazoline derivatives". supporting information. p. 8030 - 8034. Retrieved 2016/09/09.
• 2、 Dawsey, Anna C.,Li, Vincent,Hamilton, Kimberly C.,Wang, Jianmei,Williams, Travis J.. "Copper-catalyzed oxidation of azolines to azoles". experimental part. p. 7994 - 8002. Retrieved 2012/08/08.