O⁵-benzyl-N^α-tert-butyloxycarbonyl-N'-(4-cyanophenyl)-L-glutamic amide

Base Information

• Chemical Name: O⁵-benzyl-N^α-tert-butyloxycarbonyl-N'-(4-cyanophenyl)-L-glutamic amide
• CAS No.: 927191-10-4
• Molecular Formula: C₂₄H₂₇N₃O₅
• Molecular Weight: 437.495
• Mol file: 927191-10-4.mol

Synonyms:O⁵-benzyl-N^α-tert-butyloxycarbonyl-N'-(4-cyanophenyl)-L-glutamic amide

Chemical Property of O⁵-benzyl-N^α-tert-butyloxycarbonyl-N'-(4-cyanophenyl)-L-glutamic amide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of O⁵-benzyl-N^α-tert-butyloxycarbonyl-N'-(4-cyanophenyl)-L-glutamic amide

There total 3 articles about O⁵-benzyl-N^α-tert-butyloxycarbonyl-N'-(4-cyanophenyl)-L-glutamic amide 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: 90.0%

4-azidobenzonitrile (18523-41-6) + Boc-Glu(OBzl)-OH (13574-13-5) → O5-benzyl-Nα-tert-butyloxycarbonyl-N'-(4-cyanophenyl)-L-glutamic amide (927191-10-4)

Guidance literature:

Boc-Glu(OBzl)-OH; With N-methylcyclohexylamine; isopropyl chloroformate; In tetrahydrofuran; toluene; at 0 ℃; for 0.333333h;

With LiAlHSeH; In tetrahydrofuran; toluene; at 0 - 5 ℃; for 0.5h;

4-azidobenzonitrile; In tetrahydrofuran; toluene; at 25 ℃; for 3h;

DOI:10.1021/jo061703n

Reference yield:

Boc-Glu(OBzl)-OH (13574-13-5) → O5-benzyl-Nα-tert-butyloxycarbonyl-N'-(4-cyanophenyl)-L-glutamic amide (927191-10-4)

Guidance literature:

Multi-step reaction with 2 steps

1: triethylamine / tetrahydrofuran / 0.25 h / -15 °C

2: triethylamine / tetrahydrofuran / 1.) 0 deg C, 1h, 2.) RT, overnight

With triethylamine; In tetrahydrofuran;

DOI:10.1021/jm00346a013

Reference yield:

(S)-4-tert-Butoxycarbonylamino-5-isobutoxycarbonyloxy-5-oxo-pentanoic acid benzyl ester + 4-Aminobenzonitrile (873-74-5) → O5-benzyl-Nα-tert-butyloxycarbonyl-N'-(4-cyanophenyl)-L-glutamic amide (927191-10-4)

Guidance literature:

With triethylamine; In tetrahydrofuran; Yield given; 1.) 0 deg C, 1h, 2.) RT, overnight;

DOI:10.1021/jm00346a013

upstream raw materials:

4-Aminobenzonitrile

4-azidobenzonitrile

Boc-Glu(OBzl)-OH

Downstream raw materials:

trifluoroacetyl-α-L-glutamyl-p-cyanoanilide

α-L-glutamyl-p-cyanoanilide