di-tert-butyl ((Z)-{[4-(2-{2-(acetylamino)-5-[4-(methylsulfonyl)benzyl]-1,3-thiazol-4-yl}ethyl)phenyl]amino}-methylidene)biscarbamate

Base Information

• Chemical Name: di-tert-butyl ((Z)-{[4-(2-{2-(acetylamino)-5-[4-(methylsulfonyl)benzyl]-1,3-thiazol-4-yl}ethyl)phenyl]amino}-methylidene)biscarbamate
• CAS No.: 737824-55-4
• Molecular Formula: C₃₂H₄₁N₅O₇S₂
• Molecular Weight: 671.839
• Mol file: 737824-55-4.mol

Synonyms:di-tert-butyl ((Z)-{[4-(2-{2-(acetylamino)-5-[4-(methylsulfonyl)benzyl]-1,3-thiazol-4-yl}ethyl)phenyl]amino}-methylidene)biscarbamate

Chemical Property of di-tert-butyl ((Z)-{[4-(2-{2-(acetylamino)-5-[4-(methylsulfonyl)benzyl]-1,3-thiazol-4-yl}ethyl)phenyl]amino}-methylidene)biscarbamate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of di-tert-butyl ((Z)-{[4-(2-{2-(acetylamino)-5-[4-(methylsulfonyl)benzyl]-1,3-thiazol-4-yl}ethyl)phenyl]amino}-methylidene)biscarbamate

There total 14 articles about di-tert-butyl ((Z)-{[4-(2-{2-(acetylamino)-5-[4-(methylsulfonyl)benzyl]-1,3-thiazol-4-yl}ethyl)phenyl]amino}-methylidene)biscarbamate 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: 73.0%

N-{4-[2-(4-aminophenyl)ethyl]-5-[4-(methylsulfonyl)benzyl]-1,3-thiazol-2-yl}acetamide (737824-46-3) + N,N'-bis( tert-butoxycarbonyl)-1H-pyrazole-1-carboxamidine (152120-54-2,862686-58-6,1143572-00-2) → di-tert-butyl ((Z)-{[4-(2-{2-(acetylamino)-5-[4-(methylsulfonyl)benzyl]-1,3-thiazol-4-yl}ethyl)phenyl]amino}-methylidene)biscarbamate (737824-55-4)

Guidance literature:

In tetrahydrofuran; at 20 ℃; for 12h;

DOI:10.1016/j.bmc.2013.02.048

Reference yield:

ethyl 2-(acetylamino)-5-[4-(methylthio)benzyl]-1,3-thiazole-4-carboxylate (737824-50-9) → di-tert-butyl ((Z)-{[4-(2-{2-(acetylamino)-5-[4-(methylsulfonyl)benzyl]-1,3-thiazol-4-yl}ethyl)phenyl]amino}-methylidene)biscarbamate (737824-55-4)

Guidance literature:

Multi-step reaction with 6 steps

1: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / 0 - 20 °C / Inert atmosphere

2: manganese(IV) oxide / methanol; chloroform / 13 h / 20 °C / Inert atmosphere

3: potassium tert-butylate / N,N-dimethyl-formamide / 0 - 20 °C / Inert atmosphere

4: Oxone / water; tetrahydrofuran / 0 - 20 °C

5: acetic acid; palladium 10% on activated carbon; hydrogen / tetrahydrofuran; methanol / 3 h / 20 °C / 2280.15 Torr

6: tetrahydrofuran / 12 h / 20 °C

With manganese(IV) oxide; Oxone; lithium aluminium tetrahydride; palladium 10% on activated carbon; potassium tert-butylate; hydrogen; acetic acid; In tetrahydrofuran; methanol; chloroform; water; N,N-dimethyl-formamide; 3: |Wittig Olefination;

DOI:10.1016/j.bmc.2013.02.048

Reference yield:

N-{4-formyl-5-[4-(methylthio)benzyl]-1,3-thiazol-2-yl}acetamide (737824-51-0) → di-tert-butyl ((Z)-{[4-(2-{2-(acetylamino)-5-[4-(methylsulfonyl)benzyl]-1,3-thiazol-4-yl}ethyl)phenyl]amino}-methylidene)biscarbamate (737824-55-4)

Guidance literature:

Multi-step reaction with 4 steps

1: potassium tert-butylate / N,N-dimethyl-formamide / 0 - 20 °C / Inert atmosphere

2: Oxone / water; tetrahydrofuran / 0 - 20 °C

3: acetic acid; palladium 10% on activated carbon; hydrogen / tetrahydrofuran; methanol / 3 h / 20 °C / 2280.15 Torr

4: tetrahydrofuran / 12 h / 20 °C

With Oxone; palladium 10% on activated carbon; potassium tert-butylate; hydrogen; acetic acid; In tetrahydrofuran; methanol; water; N,N-dimethyl-formamide; 1: |Wittig Olefination;

DOI:10.1016/j.bmc.2013.02.048

upstream raw materials:

ethyl 2-(acetylamino)-5-[4-(methylthio)benzyl]-1,3-thiazole-4-carboxylate

N-{4-formyl-5-[4-(methylthio)benzyl]-1,3-thiazol-2-yl}acetamide

N-{5-[4-(methylsulfonyl)benzyl]-4-[2-(4-nitrophenyl)vinyl]-1,3-thiazol-2-yl}acetamide

N-{4-[2-(4-aminophenyl)ethyl]-5-[4-(methylsulfonyl)benzyl]-1,3-thiazol-2-yl}acetamide

Downstream raw materials:

N-{4-[2-(4-{[amino(imino)methyl]amino}phenyl)ethyl]-5-[4-(methylsulfonyl)benzyl]-1,3-thiazol-2-yl}acetamide