Methyl 5-methyl-2-phenyl-1,3-oxazole-4-carboxylate

Base Information

• Chemical Name: Methyl 5-methyl-2-phenyl-1,3-oxazole-4-carboxylate
• CAS No.: 100063-41-0
• Molecular Formula: C12H11NO3
• Molecular Weight: 217.224
• Hs Code.: 2934999090
• DSSTox Substance ID: DTXSID00428886
• Nikkaji Number: J1.774.820C
• Wikidata: Q82241728
• Mol file: 100063-41-0.mol

Synonyms:100063-41-0;methyl 5-methyl-2-phenyl-1,3-oxazole-4-carboxylate;5-Methyl-2-phenyloxazole-4-carboxylic Acid Methyl Ester;4-Oxazolecarboxylic acid, 5-methyl-2-phenyl-, methyl ester;5-methyl-2-phenyl-oxazole-4-carboxylic acid methyl ester;METHYL 5-METHYL-2-PHENYLOXAZOLE-4-CARBOXYLATE;SCHEMBL2778345;DTXSID00428886;AKOS025402617;TS-03111;A908373;5-Methyl-2-phenyloxazole-4-carboxylicAcidMethylEster;2-Phenyl-5-methyloxazole-4-carboxylic acid methyl ester

Chemical Property of Methyl 5-methyl-2-phenyl-1,3-oxazole-4-carboxylate

Chemical Property:

• PSA: 52.33000
• LogP: 2.43660
• XLogP3: 2.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 217.07389321
• Heavy Atom Count: 16
• Complexity: 251

Purity/Quality:

97% ^*data from raw suppliers

5-Methyl-2-phenyloxazole-4-carboxylicAcidMethylEster ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=C(N=C(O1)C2=CC=CC=C2)C(=O)OC
• Uses: 5-Methyl-2-phenyloxazole-4-carboxylic Acid Methyl Ester is an intermediate used to prepare 2-Phenyl-5-methyloxazole-4-carboxylic Acid (P336070) which is a building block used to prepare oxazole transthyretin amyloidogenesis inhibitors. 2-Phenyl-5-methyloxazole-4-carboxylic Acid is also used to synthesize inhibitors of HldE kinase as Gram-negative antivirulence drugs.

Technology Process of Methyl 5-methyl-2-phenyl-1,3-oxazole-4-carboxylate

There total 27 articles about Methyl 5-methyl-2-phenyl-1,3-oxazole-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: 96.0%

Bz-Z-ΔAbu(β-I)-OMe (1084941-24-1) → methyl 5-methyl-2-phenyloxazole-4-carboxylate (100063-41-0)

Guidance literature:

With 1,8-diazabicyclo[5.4.0]undec-7-ene; In acetonitrile; at 20 ℃; for 0.5h;

DOI:10.1016/j.tet.2010.09.014

Reference yield: 91.0%

(Z)-α-N-benzoylamino-2-butenoic acid methylester (60027-58-9) → methyl 5-methyl-2-phenyloxazole-4-carboxylate (100063-41-0)

Guidance literature:

(Z)-α-N-benzoylamino-2-butenoic acid methylester; With iodine; potassium carbonate; In tetrahydrofuran; at 80 ℃; for 3h;

With 1,8-diazabicyclo[5.4.0]undec-7-ene; In tetrahydrofuran; at 80 ℃; for 3h;

DOI:10.1002/ejoc.200800602

Reference yield: 89.0%

(Z)-N-benzoyl-β-bromo-2,3-dehydro-2-aminobutyric acid methyl ester (1242683-14-2) → methyl 5-methyl-2-phenyloxazole-4-carboxylate (100063-41-0)

Guidance literature:

With 1,8-diazabicyclo[5.4.0]undec-7-ene; In acetonitrile; at 20 ℃; for 0.5h;

DOI:10.1016/j.tet.2010.09.014

upstream raw materials:

2-benzoylamino-3-oxo-butyric acid methyl ester

2-benzoylamino-3-chloro-crotonic acid methyl ester

(E)-N-benzoyl-β-bromo-2,3-dehydro-2-aminobutyric acid methyl ester

diazomethane

Downstream raw materials:

5-methyl-2-phenyloxazole

5-methyl-2-phenyloxazole-4-carboxylic acid

Refernces

• 1、 Batsila, Christina,Kostakis, George,Hadjiarapoglou, Lazaros P. "RhII-catalyzed cycloadditions of carbomethoxy iodonium ylides". . p. 5997 - 6000. Retrieved 2002.
• 2、 Cai, Mingzhong,Tuo, Yuxin,Wei, Li,You, Shengyong. "A Highly Efficient Heterogeneous Copper-Catalyzed Oxidative Cyclization of Benzylamines and 1,3-Dicarbonyl Compounds to Give Trisubstituted Oxazoles". . p. 3091 - 3100. Retrieved 2019/08/07.
• 3、 Chen, Chengqun,Chen, Wenfu,Bao, Qianhong. "Convenient route to trisubstituted oxazoles via a copper-catalysed tandem oxidative cyclisation by oxygen oxidation". . p. 7 - 10. Retrieved 2015/02/05.