ethyl-5-(2,4-dibenzyloxy-5-isopropylphenyl)-4-iodoisoxazole-3-carboxylate

Base Information

• Chemical Name: ethyl-5-(2,4-dibenzyloxy-5-isopropylphenyl)-4-iodoisoxazole-3-carboxylate
• CAS No.: 1133784-43-6
• Molecular Formula: C₂₉H₂₈INO₅
• Molecular Weight: 597.45
• Mol file: 1133784-43-6.mol

Synonyms:ethyl-5-(2,4-dibenzyloxy-5-isopropylphenyl)-4-iodoisoxazole-3-carboxylate

Chemical Property of ethyl-5-(2,4-dibenzyloxy-5-isopropylphenyl)-4-iodoisoxazole-3-carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of ethyl-5-(2,4-dibenzyloxy-5-isopropylphenyl)-4-iodoisoxazole-3-carboxylate

There total 8 articles about ethyl-5-(2,4-dibenzyloxy-5-isopropylphenyl)-4-iodoisoxazole-3-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%

5-(2,4-bis(benzyloxy)-5-isopropylphenyl)isoxazole-3-carboxylic acid ethyl ester (747414-20-6) → ethyl-5-(2,4-dibenzyloxy-5-isopropylphenyl)-4-iodoisoxazole-3-carboxylate (1133784-43-6)

Guidance literature:

With N-iodo-succinimide; ammonium cerium (IV) nitrate; In acetonitrile; at 20 ℃;

Reference yield:

2',4'-dihydroxy-4-acetophenone (89-84-9) → ethyl-5-(2,4-dibenzyloxy-5-isopropylphenyl)-4-iodoisoxazole-3-carboxylate (1133784-43-6)

Guidance literature:

Multi-step reaction with 8 steps

1.1: potassium carbonate / acetonitrile / Reflux

2.1: potassium tert-butylate / tetrahydrofuran / 0 °C

2.2: 0 - 20 °C

3.1: palladium 10% on activated carbon; hydrogen / acetic acid; ethanol / 48 h / 20 °C / 7600.51 Torr

4.1: boron trifluoride diethyl etherate

5.1: potassium carbonate / acetonitrile / 20 °C

6.1: sodium ethanolate / ethanol / 20 °C

6.2: 20 °C

7.1: hydroxylamine hydrochloride / ethanol / 20 °C

8.1: N-iodo-succinimide; ammonium cerium (IV) nitrate / acetonitrile / 80 °C

With N-iodo-succinimide; ammonium cerium (IV) nitrate; palladium 10% on activated carbon; boron trifluoride diethyl etherate; hydroxylamine hydrochloride; potassium tert-butylate; hydrogen; sodium ethanolate; potassium carbonate; In tetrahydrofuran; ethanol; acetic acid; acetonitrile; 2.2: |Wittig Olefination / 4.1: |Friedel-Crafts Acylation;

DOI:10.1016/j.bmcl.2015.06.009

Reference yield:

(((4-(prop-1-en-2-yl)-1,3-phenylene)bis(oxy))bis(methylene))dibenzene (747414-16-0) → ethyl-5-(2,4-dibenzyloxy-5-isopropylphenyl)-4-iodoisoxazole-3-carboxylate (1133784-43-6)

Guidance literature:

Multi-step reaction with 6 steps

1.1: palladium 10% on activated carbon; hydrogen / acetic acid; ethanol / 48 h / 20 °C / 7600.51 Torr

2.1: boron trifluoride diethyl etherate

3.1: potassium carbonate / acetonitrile / 20 °C

4.1: sodium ethanolate / ethanol / 20 °C

4.2: 20 °C

5.1: hydroxylamine hydrochloride / ethanol / 20 °C

6.1: N-iodo-succinimide; ammonium cerium (IV) nitrate / acetonitrile / 80 °C

With N-iodo-succinimide; ammonium cerium (IV) nitrate; palladium 10% on activated carbon; boron trifluoride diethyl etherate; hydroxylamine hydrochloride; hydrogen; sodium ethanolate; potassium carbonate; In ethanol; acetic acid; acetonitrile; 2.1: |Friedel-Crafts Acylation;

DOI:10.1016/j.bmcl.2015.06.009

upstream raw materials:

5-(2,4-bis(benzyloxy)-5-isopropylphenyl)isoxazole-3-carboxylic acid ethyl ester

2',4'-dihydroxy-4-acetophenone

(((4-(prop-1-en-2-yl)-1,3-phenylene)bis(oxy))bis(methylene))dibenzene

2,4-bis(benzyloxy)acetophenone

Downstream raw materials:

Ethyl 5-(2,4-bis(benzyloxy)-5-isopropylphenyl)-4-(4-formylphenyl)isoxazole-3-carboxylate

Refernces

• 1、 -. "RESORCINOL DERIVATIVE AS HSP90 INHIBITOR". Paragraph 0094. . Retrieved 2017/12/27.
• 2、 -. "HSP90 INHIBITORS CONTAINING A ZINC BINDING MOIETY". Page/Page column 34; 45. . Retrieved 2009/04/24.