Carbamic acid, [5-[6-[[4-[2-oxo-2-[(triphenylmethoxy)amino]ethyl]-5-phenyl-2-thienyl]carb onyl]-2-phenyl-1H-indol-1-yl]pentyl]-, 1,1-dimethylethyl ester

Base Information

• Chemical Name: Carbamic acid, [5-[6-[[4-[2-oxo-2-[(triphenylmethoxy)amino]ethyl]-5-phenyl-2-thienyl]carb onyl]-2-phenyl-1H-indol-1-yl]pentyl]-, 1,1-dimethylethyl ester
• CAS No.: 875271-95-7
• Molecular Formula: C56H53N3O5S
• Molecular Weight: 880.12
• Mol file: 875271-95-7.mol

Synonyms:

Chemical Property of Carbamic acid, [5-[6-[[4-[2-oxo-2-[(triphenylmethoxy)amino]ethyl]-5-phenyl-2-thienyl]carb onyl]-2-phenyl-1H-indol-1-yl]pentyl]-, 1,1-dimethylethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Carbamic acid, [5-[6-[[4-[2-oxo-2-[(triphenylmethoxy)amino]ethyl]-5-phenyl-2-thienyl]carb onyl]-2-phenyl-1H-indol-1-yl]pentyl]-, 1,1-dimethylethyl ester

There total 11 articles about Carbamic acid, [5-[6-[[4-[2-oxo-2-[(triphenylmethoxy)amino]ethyl]-5-phenyl-2-thienyl]carb onyl]-2-phenyl-1H-indol-1-yl]pentyl]-, 1,1-dimethylethyl ester 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: 69.0%

2-{5-[1-(5-N-Boc-aminopentyl)-2-phenyl-1H-indol-6-carbonyl]-2-phenylthiophen-3-yl}acetic acid (875271-94-6) + O-tritylhydroxylamine (31938-11-1) → 2-{5-[1-(5-N-Boc-aminopentyl)-2-phenyl-1H-indol-6-carbonyl]-2-phenylthiophen-3-yl}-O-tritylhydroxy-acetamide (875271-95-7)

Guidance literature:

With benzotriazol-1-ol; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; In dichloromethane; at 20 ℃; for 1.5h;

DOI:10.1016/j.bmc.2005.08.018

Reference yield:

(2-phenylthiophen-3-yl)acetic acid methyl ester (875271-79-7) → 2-{5-[1-(5-N-Boc-aminopentyl)-2-phenyl-1H-indol-6-carbonyl]-2-phenylthiophen-3-yl}-O-tritylhydroxy-acetamide (875271-95-7)

Guidance literature:

Multi-step reaction with 7 steps

1: 74 percent / AlCl₃ / CH₂Cl₂ / 20 °C

2: 96 percent / stannous chloride dihydrate / ethyl acetate / 0.5 h / Heating

3: 98 percent / Et₂NH; CuI / Pd(PPh₃)4 / 4 h / 20 °C

4: 61 percent / PdCl₂(PhCN)2 / dimethylformamide / 0.5 h / 80 °C

5: 77 percent / CsF on Celite / acetonitrile / 24 h / Heating

6: 100 percent / NaOH / methanol / 4 h / Heating

7: 69 percent / HBTU; N-hydroxybenzotriazole; ethyldiisopropylamine / CH₂Cl₂ / 1.5 h / 20 °C

With sodium hydroxide; copper(l) iodide; aluminium trichloride; benzotriazol-1-ol; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; diethylamine; N-ethyl-N,N-diisopropylamine; cesium fluoride; tin(ll) chloride; bis(benzonitrile)palladium(II) dichloride; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In methanol; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; acetonitrile; 1: Friedel-Crafts reaction;

DOI:10.1016/j.bmc.2005.08.018

Reference yield:

(2-phenylthiophen-3-yl)acetic acid ethyl ester (875271-86-6) → 2-{5-[1-(5-N-Boc-aminopentyl)-2-phenyl-1H-indol-6-carbonyl]-2-phenylthiophen-3-yl}-O-tritylhydroxy-acetamide (875271-95-7)

Guidance literature:

Multi-step reaction with 9 steps

1: KOH / methanol / 3 h / Heating

2: 3.3 g / HCl / 5 h / Heating

3: 74 percent / AlCl₃ / CH₂Cl₂ / 20 °C

4: 96 percent / stannous chloride dihydrate / ethyl acetate / 0.5 h / Heating

5: 98 percent / Et₂NH; CuI / Pd(PPh₃)4 / 4 h / 20 °C

6: 61 percent / PdCl₂(PhCN)2 / dimethylformamide / 0.5 h / 80 °C

7: 77 percent / CsF on Celite / acetonitrile / 24 h / Heating

8: 100 percent / NaOH / methanol / 4 h / Heating

9: 69 percent / HBTU; N-hydroxybenzotriazole; ethyldiisopropylamine / CH₂Cl₂ / 1.5 h / 20 °C

With hydrogenchloride; potassium hydroxide; sodium hydroxide; copper(l) iodide; aluminium trichloride; benzotriazol-1-ol; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; diethylamine; N-ethyl-N,N-diisopropylamine; cesium fluoride; tin(ll) chloride; bis(benzonitrile)palladium(II) dichloride; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In methanol; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; acetonitrile; 3: Friedel-Crafts reaction;

DOI:10.1016/j.bmc.2005.08.018

upstream raw materials:

2-{5-[1-(5-N-Boc-aminopentyl)-2-phenyl-1H-indol-6-carbonyl]-2-phenylthiophen-3-yl}acetic acid

O-tritylhydroxylamine

(2-phenylthiophen-3-yl)acetic acid methyl ester

(2-phenylthiophen-3-yl)acetic acid ethyl ester

Refernces

• 1、 Park, Jewn Giew,Sill, Peter C.,Makiyi, Edward F.,Garcia-Sosa, Alfonso T.,Millard, Charles B.,Schmidt, James J.,Pang, Yuan-Ping. "Serotype-selective, small-molecule inhibitors of the zinc endopeptidase of botulinum neurotoxin serotype A". . p. 395 - 408. Retrieved 2007/10/03.