(4S,5R)-2-(2-hydroxyphenyl)-5-methyl-4,5-dihydro-oxazole-4-carboxylic acid

Base Information

• Chemical Name: (4S,5R)-2-(2-hydroxyphenyl)-5-methyl-4,5-dihydro-oxazole-4-carboxylic acid
• CAS No.: 89965-54-8
• Molecular Formula: C₁₁H₁₁NO₄
• Molecular Weight: 221.213
• Mol file: 89965-54-8.mol

Synonyms:(4S,5R)-2-(2-hydroxyphenyl)-5-methyl-4,5-dihydro-oxazole-4-carboxylic acid

Chemical Property of (4S,5R)-2-(2-hydroxyphenyl)-5-methyl-4,5-dihydro-oxazole-4-carboxylic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (4S,5R)-2-(2-hydroxyphenyl)-5-methyl-4,5-dihydro-oxazole-4-carboxylic acid

There total 11 articles about (4S,5R)-2-(2-hydroxyphenyl)-5-methyl-4,5-dihydro-oxazole-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: 99.0%

(4S,5R)-2-(2-hydroxyphenyl)-5-methyl-4,5-dihydro-oxazole-4-carboxylic acid methyl ester (89965-55-9) → (4S,5R)-2-(2-hydroxyphenyl)-5-methyl-4,5-dihydro-oxazole-4-carboxylic acid (89965-54-8)

Guidance literature:

With lithium hydroxide; In methanol; at 20 ℃; for 2.5h;

DOI:10.1002/adsc.200600550

Reference yield: 71.0%

C25H23NO4 (434953-01-2) → (4S,5R)-2-(2-hydroxyphenyl)-5-methyl-4,5-dihydro-oxazole-4-carboxylic acid (89965-54-8)

Guidance literature:

With 10% Pd/C; hydrogen; In ethanol; for 1.5h;

DOI:10.1021/ja804499r

Reference yield:

salicylic acid (69-72-7,25496-36-0,8052-31-1) → (4S,5R)-2-(2-hydroxyphenyl)-5-methyl-4,5-dihydro-oxazole-4-carboxylic acid (89965-54-8)

Guidance literature:

Multi-step reaction with 3 steps

1: 89 percent / HOBt; Et₃N; WSCl*HCl / CH₂Cl₂ / 12 h / 6 °C

2: 79 percent / 3,5-bis(trifluoromethyl)benzoic acid / MoO₂(acac)2 / toluene / 12 h / Heating

3: 99 percent / aq. LiOH / methanol / 2.5 h / 20 °C

With lithium hydroxide; WSCl*HCl; benzotriazol-1-ol; triethylamine; bis(acetylacetonato)dioxidomolybdenum(VI); In methanol; dichloromethane; toluene;

DOI:10.1002/adsc.200600550

upstream raw materials:

(4R,5R)-2-(2-hydroxyphenyl)-4-methoxycarbonyl-5-methyl-4,5-dihydro-oxazole

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

salicylic acid

2-benzyloxybenzoic acid

Downstream raw materials:

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

(4S,5R)-N-<3-(benzyloxycarbonylamino)propyl>-N-<4-(benzyloxycarbonylamino)butyl>-2-(2-hydroxyphenyl)-5-methyl-4,5-dihydro-oxazole-4-carboxamide

parabactin