4-Oxazolecarboxylic acid, 4,5-dihydro-4-(hydroxyphenylmethyl)-5-methyl-2-phenyl-, methyl ester

Base Information

• Chemical Name: 4-Oxazolecarboxylic acid, 4,5-dihydro-4-(hydroxyphenylmethyl)-5-methyl-2-phenyl-, methyl ester
• CAS No.: 114041-62-2
• Molecular Formula: C₁₉H₁₉NO₄
• Molecular Weight: 325.364
• Mol file: 114041-62-2.mol

Synonyms:

Chemical Property of 4-Oxazolecarboxylic acid, 4,5-dihydro-4-(hydroxyphenylmethyl)-5-methyl-2-phenyl-, methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 4-Oxazolecarboxylic acid, 4,5-dihydro-4-(hydroxyphenylmethyl)-5-methyl-2-phenyl-, methyl ester

There total 3 articles about 4-Oxazolecarboxylic acid, 4,5-dihydro-4-(hydroxyphenylmethyl)-5-methyl-2-phenyl-, methyl ester 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: 72.0%

benzaldehyde (100-52-7) + Lithium; methoxy-[(S)-5-methyl-2-phenyl-oxazol-(4E)-ylidene]-methanolate (88318-67-6,88318-68-7) → (R)-4-(Hydroxy-phenyl-methyl)-5-methyl-2-phenyl-4,5-dihydro-oxazole-4-carboxylic acid methyl ester (88318-78-9,88318-79-0,114041-62-2,114041-63-3,114057-10-2)

Guidance literature:

In tetrahydrofuran; Title compound not separated from byproducts; 1.) -75 deg C, 4 h 2.) 0 deg C, overnight. 70percent ds;

DOI:10.1016/S0040-4039(00)86256-5

Reference yield:

N-benzoyl-L-threonine methyl ester (79893-89-3) → (R)-4-(Hydroxy-phenyl-methyl)-5-methyl-2-phenyl-4,5-dihydro-oxazole-4-carboxylic acid methyl ester (88318-78-9,88318-79-0,114041-62-2,114041-63-3,114057-10-2)

Guidance literature:

Multi-step reaction with 3 steps

1: 84 percent / SOCl₂ / 98.4percent ds

2: LDA / tetrahydrofuran / -75 °C

3: 72 percent / tetrahydrofuran / 1.) -75 deg C, 4 h 2.) 0 deg C, overnight. 70percent ds

With thionyl chloride; lithium diisopropyl amide; In tetrahydrofuran;

DOI:10.1016/S0040-4039(00)86256-5

Reference yield:

(4S,5S)-5-methyl-2-phenyl-4,5-dihydro-oxazole-4-carboxylic acid methyl ester (82659-84-5) → (R)-4-(Hydroxy-phenyl-methyl)-5-methyl-2-phenyl-4,5-dihydro-oxazole-4-carboxylic acid methyl ester (88318-78-9,88318-79-0,114041-62-2,114041-63-3,114057-10-2)

Guidance literature:

Multi-step reaction with 2 steps

1: LDA / tetrahydrofuran / -75 °C

2: 72 percent / tetrahydrofuran / 1.) -75 deg C, 4 h 2.) 0 deg C, overnight. 70percent ds

With lithium diisopropyl amide; In tetrahydrofuran;

DOI:10.1016/S0040-4039(00)86256-5

upstream raw materials:

benzaldehyde

Lithium; methoxy-[(S)-5-methyl-2-phenyl-oxazol-(4E)-ylidene]-methanolate

N-benzoyl-L-threonine methyl ester

(4S,5S)-5-methyl-2-phenyl-4,5-dihydro-oxazole-4-carboxylic acid methyl ester

Refernces