1-Tert-butyl 2-(4-nitrophenyl) pyrrolidine-1,2-dicarboxylate

Base Information

• Chemical Name: 1-Tert-butyl 2-(4-nitrophenyl) pyrrolidine-1,2-dicarboxylate
• CAS No.: 28310-65-8
• Molecular Formula: C16H20N2O6
• Molecular Weight: 336.345
• Hs Code.: 2933990090
• NSC Number: 164055
• DSSTox Substance ID: DTXSID90304049
• Mol file: 28310-65-8.mol

Synonyms:28310-65-8;1-tert-butyl 2-(4-nitrophenyl) pyrrolidine-1,2-dicarboxylate;NSC164055;DTXSID90304049;1-O-tert-butyl 2-O-(4-nitrophenyl) pyrrolidine-1,2-dicarboxylate;NSC-164055;FT-0772690

Chemical Property of 1-Tert-butyl 2-(4-nitrophenyl) pyrrolidine-1,2-dicarboxylate

Chemical Property:

• Vapor Pressure: 8.96E-09mmHg at 25°C
• Refractive Index: 1.555
• Boiling Point: 463.6 °C at 760 mmHg
• PKA: -3.87±0.40(Predicted)
• Flash Point: 234.2 °C
• PSA: 101.66000
• Density: 1.284 g/cm³
• LogP: 3.36080
• Storage Temp.: -15°C
• XLogP3: 2.9
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 5
• Exact Mass: 336.13213636
• Heavy Atom Count: 24
• Complexity: 488

Purity/Quality:

99% ^*data from raw suppliers

Boc-L-proline 4-nitrophenyl ester ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)N1CCCC1C(=O)OC2=CC=C(C=C2)[N+](=O)[O-]

Technology Process of 1-Tert-butyl 2-(4-nitrophenyl) pyrrolidine-1,2-dicarboxylate

There total 2 articles about 1-Tert-butyl 2-(4-nitrophenyl) pyrrolidine-1,2-dicarboxylate 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:

4-nitro-phenol (100-02-7,78813-13-5,89830-32-0) + 1-(tert-butoxycarbonyl)-L-proline (15761-39-4,59433-50-0) → N-tert-butyloxycarbonyl-proline p-nitrophenyl ester (28310-65-8)

Guidance literature:

DOI:10.1021/ja804993y

Reference yield:

L-proline (147-85-3,25191-13-3,37159-97-0,4305-67-3,4607-28-7) → N-tert-butyloxycarbonyl-proline p-nitrophenyl ester (28310-65-8)

Guidance literature:

Multi-step reaction with 2 steps

1: triethylamine / dichloromethane / 3 h / 0 °C

2: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 12 h / 25 °C

With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; In dichloromethane;

DOI:10.1007/s00210-020-01868-4

Reference yield: 95.4%

N-tert-butyloxycarbonyl-proline p-nitrophenyl ester (28310-65-8) + H-Val-Thr-Leu-Asp(OBzl)-Leu-Arg(NO2)-Tyr-OMe*TFA → Boc-Pro-Val-Thr-Leu-Asp(OBzl)-Leu-Arg(NO2)-Tyr-OMe (133463-32-8)

Guidance literature:

With triethylamine; In N,N-dimethyl-formamide; Ambient temperature;

DOI:10.1248/cpb.38.3249

upstream raw materials:

4-nitro-phenol

1-(tert-butoxycarbonyl)-L-proline

L-proline

Downstream raw materials:

Boc-L-Pro-L-Asp(Bzl)-NH₂

Boc-Pro-Glu(OBzl)-Gly-OMe

Boc-PGG-OCH₂Ph

Boc-Pro-Val-Thr-Leu-Asp(OBzl)-Leu-Arg(NO₂)-Tyr-OMe