(2,5-dioxopyrrolidin-1-yl) 3-(1H-indol-3-yl)-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoate

Base Information

• Chemical Name: (2,5-dioxopyrrolidin-1-yl) 3-(1H-indol-3-yl)-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoate
• CAS No.: 3392-11-8
• Molecular Formula: C20H23N3O6
• Molecular Weight: 401.419
• NSC Number: 164059
• Mol file: 3392-11-8.mol

Synonyms:(2,5-dioxopyrrolidin-1-yl) 3-(1H-indol-3-yl)-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoate;NSC164059;SCHEMBL3796578;(2,5-dioxopyrrolidin-1-yl) (2S)-3-(1H-indol-3-yl)-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoate;NSC-164059;FT-0634782;N-Boc-L-tryptophan N-hydroxysuccinimide ester

Chemical Property of (2,5-dioxopyrrolidin-1-yl) 3-(1H-indol-3-yl)-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoate

Chemical Property:

• Melting Point: 146-148 °C
• Refractive Index: 1.615
• PSA: 117.80000
• Density: 1.35 g/cm³
• LogP: 2.53970
• Storage Temp.: −20°C
• XLogP3: 1.9
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 8
• Exact Mass: 401.15868546
• Heavy Atom Count: 29
• Complexity: 658

Purity/Quality:

99% ^*data from raw suppliers

Boc-Trp-OSu ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)NC(CC1=CNC2=CC=CC=C21)C(=O)ON3C(=O)CCC3=O

Technology Process of (2,5-dioxopyrrolidin-1-yl) 3-(1H-indol-3-yl)-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoate

There total 4 articles about (2,5-dioxopyrrolidin-1-yl) 3-(1H-indol-3-yl)-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoate 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: 89.0%

Boc-Trp-OH (13139-14-5) + 1,2,2,2-tetrachloroethyl-(N-succinimidyl)carbonate (107960-02-1) → 2,5-dioxopyrrolidin-1-yl N-(tert-butoxycarbonyl)-L-tryptophanate (3392-11-8)

Guidance literature:

With 4-methyl-morpholine; In tetrahydrofuran; acetonitrile; Ambient temperature;

DOI:10.1021/jo00388a005

Reference yield: 83.0%

1-hydroxy-pyrrolidine-2,5-dione (6066-82-6) + Boc-Trp-OH (13139-14-5) → 2,5-dioxopyrrolidin-1-yl N-(tert-butoxycarbonyl)-L-tryptophanate (3392-11-8)

Guidance literature:

With dicyclohexyl-carbodiimide; In ethyl acetate; at 35 ℃; for 15h;

DOI:10.1021/acs.chemrestox.5b00047

Reference yield:

di-tert-butyl dicarbonate (24424-99-5) → 2,5-dioxopyrrolidin-1-yl N-(tert-butoxycarbonyl)-L-tryptophanate (3392-11-8)

Guidance literature:

Multi-step reaction with 2 steps

1: Amberlyst? - 15 / ethanol / 40 - 45 °C

2: dicyclohexyl-carbodiimide / acetonitrile / 0.25 h / 20 °C / Inert atmosphere

With dicyclohexyl-carbodiimide; In ethanol; acetonitrile;

DOI:10.1002/chem.201303865

upstream raw materials:

1-hydroxy-pyrrolidine-2,5-dione

Boc-Trp-OH

1,2,2,2-tetrachloroethyl-(N-succinimidyl)carbonate

di-tert-butyl dicarbonate

Downstream raw materials:

(S)-methyl 2-((S)-2-((tert-butoxycarbonyl)amino)-3-(1H-indol-3-yl)propanamido)-3-methylbutanoate

cyclo[Arg-Gly-Asp-D-Tyr-Lys(Boc-Trp)]

cyclo[Arg-Gly-Asp-D-Tyr-Lys(Trp)]

cyclo[Arg-Gly-Asp-D-Tyr-Lys(Trp)] monohydrochloride