N-fluorenylmethoxycarbonyl-L-prolyl-2-(tert-butyloxycarbonylaminomethyl)-5-chlorobenzylamide

Base Information

• Chemical Name: N-fluorenylmethoxycarbonyl-L-prolyl-2-(tert-butyloxycarbonylaminomethyl)-5-chlorobenzylamide
• CAS No.: 439117-43-8
• Molecular Formula: C₃₃H₃₆ClN₃O₅
• Molecular Weight: 590.119
• Mol file: 439117-43-8.mol

Synonyms:N-fluorenylmethoxycarbonyl-L-prolyl-2-(tert-butyloxycarbonylaminomethyl)-5-chlorobenzylamide

Chemical Property of N-fluorenylmethoxycarbonyl-L-prolyl-2-(tert-butyloxycarbonylaminomethyl)-5-chlorobenzylamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N-fluorenylmethoxycarbonyl-L-prolyl-2-(tert-butyloxycarbonylaminomethyl)-5-chlorobenzylamide

There total 7 articles about N-fluorenylmethoxycarbonyl-L-prolyl-2-(tert-butyloxycarbonylaminomethyl)-5-chlorobenzylamide 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: 94.0%

Fmoc-Pro-OH (71989-31-6) + 2-(tert-butyloxycarbonylaminomethyl)-5-chlorobenzylamine (439116-15-1) → N-fluorenylmethoxycarbonyl-L-prolyl-2-(tert-butyloxycarbonylaminomethyl)-5-chlorobenzylamide (439117-43-8)

Guidance literature:

With 1-hydroxybenzotriazol-hydrate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In N,N-dimethyl-formamide; for 2h; pH=6;

DOI:10.1021/jm049423s

Reference yield:

di-tert-butyl dicarbonate (24424-99-5) → N-fluorenylmethoxycarbonyl-L-prolyl-2-(tert-butyloxycarbonylaminomethyl)-5-chlorobenzylamide (439117-43-8)

Guidance literature:

Multi-step reaction with 4 steps

1: tetrahydrofuran

2: DPPA / toluene

3: PPh₃; H₂O / tetrahydrofuran

4: EDCI; HOBT; i-Pr₂NEt / dimethylformamide

With diphenyl-phosphinic acid; water; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; triphenylphosphine; In tetrahydrofuran; N,N-dimethyl-formamide; toluene;

DOI:10.1016/j.bmcl.2004.06.030

Reference yield:

methyl-2-bromo-5-chlorobenzoate (27007-53-0) → N-fluorenylmethoxycarbonyl-L-prolyl-2-(tert-butyloxycarbonylaminomethyl)-5-chlorobenzylamide (439117-43-8)

Guidance literature:

Multi-step reaction with 6 steps

1: Pd(PPh₃)4 / dimethylformamide / 60 °C

2: LiAlH₄ / tetrahydrofuran

3: tetrahydrofuran

4: DPPA / toluene

5: PPh₃; H₂O / tetrahydrofuran

6: EDCI; HOBT; i-Pr₂NEt / dimethylformamide

With lithium aluminium tetrahydride; tetrakis(triphenylphosphine) palladium⁽⁰⁾; diphenyl-phosphinic acid; water; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; triphenylphosphine; In tetrahydrofuran; N,N-dimethyl-formamide; toluene;

DOI:10.1016/j.bmcl.2004.06.030

upstream raw materials:

Fmoc-Pro-OH

2-(tert-butyloxycarbonylaminomethyl)-5-chlorobenzylamine

di-tert-butyl dicarbonate

methyl-2-bromo-5-chlorobenzoate

Downstream raw materials:

(S)-tert-butyl 4-chloro-2-((pyrrolidine-2-carboxamido)methyl)benzylcarbamate

9-hydroxy-9-fluorenylcarbonyl-L-prolyl-2-(tert-butyloxycarbonylaminomethyl)-5-chlorobenzylamide

4-aza-9-hydroxy-9-fluorenylcarbonyl-L-prolyl-2-(tert-butyloxycarbonylaminomethyl)-5-chlorobenzylamide

3-aza-9-hydroxy-9-fluorenylcarbonyl-L-prolyl-2-(tert-butyloxycarbonylaminomethyl)-5-chlorobenzylamide