methyl (+/-)-1-[(N-2-chloroallyl-N-benzyloxycarbamoyl)methyl]-5-ethyl-2-methoxycyclohexa-2,5-diene carboxylate

Base Information

• Chemical Name: methyl (+/-)-1-[(N-2-chloroallyl-N-benzyloxycarbamoyl)methyl]-5-ethyl-2-methoxycyclohexa-2,5-diene carboxylate
• CAS No.: 881897-27-4
• Molecular Formula: C₂₃H₂₆ClNO₆
• Molecular Weight: 447.916
• Mol file: 881897-27-4.mol

Synonyms:methyl (+/-)-1-[(N-2-chloroallyl-N-benzyloxycarbamoyl)methyl]-5-ethyl-2-methoxycyclohexa-2,5-diene carboxylate

Chemical Property of methyl (+/-)-1-[(N-2-chloroallyl-N-benzyloxycarbamoyl)methyl]-5-ethyl-2-methoxycyclohexa-2,5-diene carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl (+/-)-1-[(N-2-chloroallyl-N-benzyloxycarbamoyl)methyl]-5-ethyl-2-methoxycyclohexa-2,5-diene carboxylate

There total 3 articles about methyl (+/-)-1-[(N-2-chloroallyl-N-benzyloxycarbamoyl)methyl]-5-ethyl-2-methoxycyclohexa-2,5-diene 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: 81.0%

1-{[(2-chloro-allyl)-hydroxy-carbamoyl]-methyl}-5-ethyl-2-methoxy-cyclohexa-2,5-dienecarboxylic acid methyl ester + benzoyl chloride (98-88-4) → methyl (+/-)-1-[(N-2-chloroallyl-N-benzyloxycarbamoyl)methyl]-5-ethyl-2-methoxycyclohexa-2,5-diene carboxylate (881897-27-4)

Guidance literature:

With triethylamine; In dichloromethane; at 20 ℃; for 0.25h;

DOI:10.1021/ol052749q

Reference yield:

(+/-)-2-(1-(methoxycarbonyl)-5-ethyl-2-methoxycyclohexa-2,5-dienyl)acetic acid (881897-25-2) → methyl (+/-)-1-[(N-2-chloroallyl-N-benzyloxycarbamoyl)methyl]-5-ethyl-2-methoxycyclohexa-2,5-diene carboxylate (881897-27-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 69 percent / EDC / tetrahydrofuran; H₂O / 2 h / 20 °C / pH 5

2: 81 percent / Et₃N / CH₂Cl₂ / 0.25 h / 20 °C

With N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; triethylamine; In tetrahydrofuran; dichloromethane; water;

DOI:10.1021/ol052749q

Reference yield:

(+/-)-methyl 5-ethyl-2-methoxy-1-(tert-butoxycarbonylmethyl)cyclohexa-2,5-dienecarboxylate (881897-24-1) → methyl (+/-)-1-[(N-2-chloroallyl-N-benzyloxycarbamoyl)methyl]-5-ethyl-2-methoxycyclohexa-2,5-diene carboxylate (881897-27-4)

Guidance literature:

Multi-step reaction with 3 steps

1: 98 percent / TMSOTf; 2,6-lutidine / CH₂Cl₂ / 1 h

2: 69 percent / EDC / tetrahydrofuran; H₂O / 2 h / 20 °C / pH 5

3: 81 percent / Et₃N / CH₂Cl₂ / 0.25 h / 20 °C

With 2,6-dimethylpyridine; trimethylsilyl trifluoromethanesulfonate; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; triethylamine; In tetrahydrofuran; dichloromethane; water;

DOI:10.1021/ol052749q

upstream raw materials:

benzoyl chloride

(+/-)-2-(1-(methoxycarbonyl)-5-ethyl-2-methoxycyclohexa-2,5-dienyl)acetic acid

(+/-)-methyl 5-ethyl-2-methoxy-1-(tert-butoxycarbonylmethyl)cyclohexa-2,5-dienecarboxylate

Downstream raw materials:

methyl 5-ethyl-2-methoxybenzoate