methyl 4-[(2-(acetylamino)-4-{2-[4-({(Z)-[(tert-butoxycarbonyl)amino][(tert-butoxycarbonyl)imino]methyl}-amino)phenyl]ethyl}-1,3-thiazol-5-yl)methyl]benzoate

Base Information

• Chemical Name: methyl 4-[(2-(acetylamino)-4-{2-[4-({(Z)-[(tert-butoxycarbonyl)amino][(tert-butoxycarbonyl)imino]methyl}-amino)phenyl]ethyl}-1,3-thiazol-5-yl)methyl]benzoate
• CAS No.: 737825-29-5
• Molecular Formula: C₃₃H₄₁N₅O₇S
• Molecular Weight: 651.784

Synonyms:

Chemical Property of methyl 4-[(2-(acetylamino)-4-{2-[4-({(Z)-[(tert-butoxycarbonyl)amino][(tert-butoxycarbonyl)imino]methyl}-amino)phenyl]ethyl}-1,3-thiazol-5-yl)methyl]benzoate

Chemical Property:

Purity/Quality:

Safty Information:

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Technology Process of methyl 4-[(2-(acetylamino)-4-{2-[4-({(Z)-[(tert-butoxycarbonyl)amino][(tert-butoxycarbonyl)imino]methyl}-amino)phenyl]ethyl}-1,3-thiazol-5-yl)methyl]benzoate

There total 13 articles about methyl 4-[(2-(acetylamino)-4-{2-[4-({(Z)-[(tert-butoxycarbonyl)amino][(tert-butoxycarbonyl)imino]methyl}-amino)phenyl]ethyl}-1,3-thiazol-5-yl)methyl]benzoate 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: 83.0%

methyl 4-({2-(acetylamino)-4-[2-(4-aminophenyl)ethyl]-1,3-thiazol-5-yl}methyl)benzoate (737825-28-4) + N,N'-bis( tert-butoxycarbonyl)-1H-pyrazole-1-carboxamidine (152120-54-2,862686-58-6,1143572-00-2) → methyl 4-[(2-(acetylamino)-4-{2-[4-({(Z)-[(tert-butoxycarbonyl)amino][(tert-butoxycarbonyl)imino]methyl}-amino)phenyl]ethyl}-1,3-thiazol-5-yl)methyl]benzoate (737825-29-5,776327-07-2)

Guidance literature:

In tetrahydrofuran; at 20 ℃; for 17h; Inert atmosphere;

DOI:10.1016/j.bmc.2013.02.048

Reference yield:

ethyl 2-amino-5-(4-iodobenzyl)-1,3-thiazole-4-carboxylate hydrobromide (737825-22-8) → methyl 4-[(2-(acetylamino)-4-{2-[4-({(Z)-[(tert-butoxycarbonyl)amino][(tert-butoxycarbonyl)imino]methyl}-amino)phenyl]ethyl}-1,3-thiazol-5-yl)methyl]benzoate (737825-29-5,776327-07-2)

Guidance literature:

Multi-step reaction with 7 steps

1: pyridine / dichloromethane / 0 - 20 °C / Inert atmosphere

2: lithium borohydride / tetrahydrofuran / 0 °C / Inert atmosphere; Reflux

3: manganese(IV) oxide / methanol; chloroform / 34 h / 20 °C / Inert atmosphere

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

5: palladium diacetate; triethylamine; 1,3-bis-(diphenylphosphino)propane / N,N-dimethyl-formamide / 6.5 h / 20 - 70 °C

6: palladium 10% on activated carbon; hydrogen / tetrahydrofuran; methanol / 1 h / 20 °C / 1140.08 Torr

7: tetrahydrofuran / 17 h / 20 °C / Inert atmosphere

With pyridine; manganese(IV) oxide; lithium borohydride; palladium 10% on activated carbon; 1,3-bis-(diphenylphosphino)propane; potassium tert-butylate; hydrogen; palladium diacetate; triethylamine; In tetrahydrofuran; methanol; dichloromethane; chloroform; N,N-dimethyl-formamide;

DOI:10.1016/j.bmc.2013.02.048

Reference yield:

ethyl 2-(acetylamino)-5-(4-iodobenzyl)-1,3-thiazole-4-carboxylate (737825-23-9) → methyl 4-[(2-(acetylamino)-4-{2-[4-({(Z)-[(tert-butoxycarbonyl)amino][(tert-butoxycarbonyl)imino]methyl}-amino)phenyl]ethyl}-1,3-thiazol-5-yl)methyl]benzoate (737825-29-5,776327-07-2)

Guidance literature:

Multi-step reaction with 6 steps

1: lithium borohydride / tetrahydrofuran / 0 °C / Inert atmosphere; Reflux

2: manganese(IV) oxide / methanol; chloroform / 34 h / 20 °C / Inert atmosphere

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

4: palladium diacetate; triethylamine; 1,3-bis-(diphenylphosphino)propane / N,N-dimethyl-formamide / 6.5 h / 20 - 70 °C

5: palladium 10% on activated carbon; hydrogen / tetrahydrofuran; methanol / 1 h / 20 °C / 1140.08 Torr

6: tetrahydrofuran / 17 h / 20 °C / Inert atmosphere

With manganese(IV) oxide; lithium borohydride; palladium 10% on activated carbon; 1,3-bis-(diphenylphosphino)propane; potassium tert-butylate; hydrogen; palladium diacetate; triethylamine; In tetrahydrofuran; methanol; chloroform; N,N-dimethyl-formamide;

DOI:10.1016/j.bmc.2013.02.048

upstream raw materials:

ethyl 4-(4-iodophenyl)-2-oxobutanoate

ethyl 3-bromo-4-(4-iodophenyl)-2-oxobutanoate

ethyl 2-amino-5-(4-iodobenzyl)-1,3-thiazole-4-carboxylate hydrobromide

ethyl 2-(acetylamino)-5-(4-iodobenzyl)-1,3-thiazole-4-carboxylate

Downstream raw materials:

methyl 4-({2-(acetylamino)-4-[2-(4-{[amino(imino)methyl]amino}phenyl)ethyl]-1,3-thiazol-5-yl}methyl)benzoate hydrochloride

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