N-[(9-fluorenyl)methoxycarbonyl]-p-[3-(trifluoromethyl)diaziridine]-L-phenylalanine tert-butyl ester

Base Information

• Chemical Name: N-[(9-fluorenyl)methoxycarbonyl]-p-[3-(trifluoromethyl)diaziridine]-L-phenylalanine tert-butyl ester
• CAS No.: 886583-24-0
• Molecular Formula: C₃₀H₃₀F₃N₃O₄
• Molecular Weight: 553.581
• Mol file: 886583-24-0.mol

Synonyms:N-[(9-fluorenyl)methoxycarbonyl]-p-[3-(trifluoromethyl)diaziridine]-L-phenylalanine tert-butyl ester

Chemical Property of N-[(9-fluorenyl)methoxycarbonyl]-p-[3-(trifluoromethyl)diaziridine]-L-phenylalanine tert-butyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N-[(9-fluorenyl)methoxycarbonyl]-p-[3-(trifluoromethyl)diaziridine]-L-phenylalanine tert-butyl ester

There total 7 articles about N-[(9-fluorenyl)methoxycarbonyl]-p-[3-(trifluoromethyl)diaziridine]-L-phenylalanine tert-butyl 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: 55.0%

3-(p-iodophenyl)-3-(trifluoromethyl)diaziridine (210107-37-2) + (2R)-2-(9H-Fluoren-9-ylmethoxycarbonylamino)-3-iodopropionic acid tert-butyl ester (282734-33-2) → N-[(9-fluorenyl)methoxycarbonyl]-p-[3-(trifluoromethyl)diaziridine]-L-phenylalanine tert-butyl ester (886583-24-0)

Guidance literature:

(2R)-2-(9H-Fluoren-9-ylmethoxycarbonylamino)-3-iodopropionic acid tert-butyl ester; With zinc; In N,N-dimethyl-formamide; at 20 ℃; for 0.5h;

3-(p-iodophenyl)-3-(trifluoromethyl)diaziridine; With tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; tris-(o-tolyl)phosphine; In N,N-dimethyl-formamide; at 20 ℃; for 1h;

DOI:10.1021/jm050958a

Reference yield:

N-(9H-fluoren-9-ylmethoxycarbonyl)-L-serine (73724-45-5) → N-[(9-fluorenyl)methoxycarbonyl]-p-[3-(trifluoromethyl)diaziridine]-L-phenylalanine tert-butyl ester (886583-24-0)

Guidance literature:

Multi-step reaction with 3 steps

1.1: dicyclohexylcarbodiimide; copper(I) chloride / 72 h / 20 °C

1.2: 67 percent / CH₂Cl₂ / 2 h / 20 °C

2.1: 88 percent / methyltriphenoxyphosphonium iodide / dimethylformamide / 1 h / 20 °C

3.1: Zn / dimethylformamide / 0.5 h / 20 °C

3.2: 55 percent / tris(dibenzylideneacetone)dipalladium⁽⁰⁾; tri-o-tolylphosphine / dimethylformamide / 1 h / 20 °C

With methyltriphenoxyphosphonium iodide; dicyclohexyl-carbodiimide; copper(l) chloride; zinc; In N,N-dimethyl-formamide;

DOI:10.1021/jm050958a

Reference yield:

para-diiodobenzene (624-38-4,1032416-46-8) → N-[(9-fluorenyl)methoxycarbonyl]-p-[3-(trifluoromethyl)diaziridine]-L-phenylalanine tert-butyl ester (886583-24-0)

Guidance literature:

Multi-step reaction with 5 steps

1.1: 81 percent / n-BuLi / diethyl ether / 4 h / -78 - 20 °C

2.1: 94 percent / NH₂OH*HCl; pyridine / ethanol / 2 h / Heating

3.1: 94 percent / pyridine / 2 h / Heating

4.1: 96 percent / NH₃ / diethyl ether / 16 h / -78 - 20 °C

5.1: Zn / dimethylformamide / 0.5 h / 20 °C

5.2: 55 percent / tris(dibenzylideneacetone)dipalladium⁽⁰⁾; tri-o-tolylphosphine / dimethylformamide / 1 h / 20 °C

With pyridine; n-butyllithium; hydroxylamine hydrochloride; ammonia; zinc; In diethyl ether; ethanol; N,N-dimethyl-formamide;

DOI:10.1021/jm050958a

upstream raw materials:

3-(p-iodophenyl)-3-(trifluoromethyl)diaziridine

(2R)-2-(9H-Fluoren-9-ylmethoxycarbonylamino)-3-iodopropionic acid tert-butyl ester

para-diiodobenzene

2,2,2-trifluoro-1-(4-iodophenyl)ethan-1-one

Downstream raw materials:

(S)-N-(9-fluorenylmethoxycarbonyl)-[4-[3-(trifluoromethyl)-3H-diazirin-3-yl]phenyl]alanine

N-[(9-fluorenyl)methoxycarbonyl]-p-[3-(trifluoromethyl)-3H-diazirin-3-yl]-L-phenylalanine tert-butyl ester

Refernces