trans-2,5-dioxo-1-pyrrolidinyl 4-{[[(2E)-4-[(2,5-dioxo-1-pyrrolidinyl)oxy]-1,4-dioxo-2-buten-1-yl]amino]methyl}tranexamate

Base Information

• Chemical Name: trans-2,5-dioxo-1-pyrrolidinyl 4-{[[(2E)-4-[(2,5-dioxo-1-pyrrolidinyl)oxy]-1,4-dioxo-2-buten-1-yl]amino]methyl}tranexamate
• CAS No.: 1337538-63-2
• Molecular Formula: C₂₀H₂₃N₃O₉
• Molecular Weight: 449.417
• Mol file: 1337538-63-2.mol

Synonyms:trans-2,5-dioxo-1-pyrrolidinyl 4-{[[(2E)-4-[(2,5-dioxo-1-pyrrolidinyl)oxy]-1,4-dioxo-2-buten-1-yl]amino]methyl}tranexamate

Chemical Property of trans-2,5-dioxo-1-pyrrolidinyl 4-{[[(2E)-4-[(2,5-dioxo-1-pyrrolidinyl)oxy]-1,4-dioxo-2-buten-1-yl]amino]methyl}tranexamate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of trans-2,5-dioxo-1-pyrrolidinyl 4-{[[(2E)-4-[(2,5-dioxo-1-pyrrolidinyl)oxy]-1,4-dioxo-2-buten-1-yl]amino]methyl}tranexamate

There total 3 articles about trans-2,5-dioxo-1-pyrrolidinyl 4-{[[(2E)-4-[(2,5-dioxo-1-pyrrolidinyl)oxy]-1,4-dioxo-2-buten-1-yl]amino]methyl}tranexamate 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: 98.9%

N-trifluoroacetoxy succinimide (5672-89-9) + C12H17NO5 (953817-12-4) → trans-2,5-dioxo-1-pyrrolidinyl 4-{[[(2E)-4-[(2,5-dioxo-1-pyrrolidinyl)oxy]-1,4-dioxo-2-buten-1-yl]amino]methyl}tranexamate (1337538-63-2)

Guidance literature:

at 15 - 20 ℃;

Reference yield: 94.0%

trans-4-([(2Z)-3-carboxyprop-2-enoyl]aminolmethyl)cyclohexanecarboxylic acid (69907-68-2) + 1-hydroxy-pyrrolidine-2,5-dione (6066-82-6) → trans-2,5-dioxo-1-pyrrolidinyl 4-{[[(2E)-4-[(2,5-dioxo-1-pyrrolidinyl)oxy]-1,4-dioxo-2-buten-1-yl]amino]methyl}tranexamate (1337538-63-2)

Guidance literature:

With pyridine; trifluoroacetic anhydride; In dichloromethane; at 0 - 20 ℃; Inert atmosphere;

DOI:10.1021/jo201686e

Reference yield:

trans-4-aminomethyl-cyclohexyl-carboxylic acid (1197-18-8) → trans-2,5-dioxo-1-pyrrolidinyl 4-{[[(2E)-4-[(2,5-dioxo-1-pyrrolidinyl)oxy]-1,4-dioxo-2-buten-1-yl]amino]methyl}tranexamate (1337538-63-2)

Guidance literature:

Multi-step reaction with 2 steps

1: acetonitrile / 6 h / 20 °C / Inert atmosphere

2: pyridine; trifluoroacetic anhydride / dichloromethane / 0 - 20 °C / Inert atmosphere

With pyridine; trifluoroacetic anhydride; In dichloromethane; acetonitrile;

DOI:10.1021/jo201686e

upstream raw materials:

trans-4-([(2Z)-3-carboxyprop-2-enoyl]aminolmethyl)cyclohexanecarboxylic acid

1-hydroxy-pyrrolidine-2,5-dione

trans-4-aminomethyl-cyclohexyl-carboxylic acid

N-trifluoroacetoxy succinimide

Downstream raw materials:

4-(N-maleimidomethyl)cyclohexanecarboxylic acid N-hydroxysuccinimide ester

Refernces

• 1、 Leonard, Nicholas M.,Brunckova, Jarmila. "In situ formation of N-trifluoroacetoxy succinimide (TFA-NHS): One-pot formation of succinimidyl esters, N-trifluoroacetyl amino acid succinimidyl esters, and N-maleoyl amino acid succinimidyl esters". experimental part. p. 9169 - 9174. Retrieved 2011/12/16.