N-[4-[2-(2-Amino-4,7-dihydro-4-oxo-3H-pyrrolo[2,3-d]pyrimidin-5-yl)ethyl]benzoyl]-L-glutamic acid 1,5-diethyl ester 4-methylbenzenesulfonate

Base Information

• Chemical Name: N-[4-[2-(2-Amino-4,7-dihydro-4-oxo-3H-pyrrolo[2,3-d]pyrimidin-5-yl)ethyl]benzoyl]-L-glutamic acid 1,5-diethyl ester 4-methylbenzenesulfonate
• CAS No.: 165049-28-5
• Molecular Formula: C24H29N5O6^.C7H8O3S
• Molecular Weight: 655.729
• Hs Code.: 2942000000
• Mol file: 165049-28-5.mol

Synonyms:D-Pemetrexed Dimethyl Diester; Pemetrexed Methyl Ester; pemetrexed dimethyl ester;

Chemical Property of N-[4-[2-(2-Amino-4,7-dihydro-4-oxo-3H-pyrrolo[2,3-d]pyrimidin-5-yl)ethyl]benzoyl]-L-glutamic acid 1,5-diethyl ester 4-methylbenzenesulfonate

Chemical Property:

• PSA: 232.01000
• LogP: 4.91800
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• Solubility.: Dichloromethane (Very Slightly), DMF (Slightly, Sonicated), DMSO (Slightly)

Purity/Quality:

99% ^*data from raw suppliers

N-[4-[2-(2-Amino-4,7-dihydro-4-oxo-3H-pyrrolo[2,3-d]pyrimidin-5-yl)ethyl]benzoyl]-L-glutamicAcid1,5-DiethylEster4-Methylbenzenesulfonate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: N-[4-[2-(2-Amino-4,7-dihydro-4-oxo-3H-pyrrolo[2,3-d]pyrimidin-5-yl)ethyl]benzoyl]-L-glutamic Acid, referred to as Pemetrexed, is used in the treatment of malignant pleural mesothelioma (MPM).

Technology Process of N-[4-[2-(2-Amino-4,7-dihydro-4-oxo-3H-pyrrolo[2,3-d]pyrimidin-5-yl)ethyl]benzoyl]-L-glutamic acid 1,5-diethyl ester 4-methylbenzenesulfonate

There total 18 articles about N-[4-[2-(2-Amino-4,7-dihydro-4-oxo-3H-pyrrolo[2,3-d]pyrimidin-5-yl)ethyl]benzoyl]-L-glutamic acid 1,5-diethyl ester 4-methylbenzenesulfonate 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: 85.0%

4-(2-(2-amino-4-oxo-4,7-dihydro-1H-pyrrolo[2,3-d]pyrimidin-5-yl)ethyl)benzoic acid + diethyl-L-glutamate hydrochloride (1118-89-4) + toluene-4-sulfonic acid (104-15-4) → pemetrexed diethyl ester p-toluenesulfonic acid salt (165049-28-5)

Guidance literature:

diethyl-L-glutamate hydrochloride; With sodium hydrogencarbonate; In dichloromethane; N,N-dimethyl-formamide; at 20 ℃; for 0.5h;

4-(2-(2-amino-4-oxo-4,7-dihydro-1H-pyrrolo[2,3-d]pyrimidin-5-yl)ethyl)benzoic acid; With 4-methyl-morpholine; 2-chloro-4,6-dimethoxy-1 ,3,5-triazine; at 0 - 15 ℃; for 1h;

toluene-4-sulfonic acid; In ethanol; N,N-dimethyl-formamide; at 50 ℃; for 2h;

Reference yield: 68.1%

diethyl-L-glutamate hydrochloride (1118-89-4) + toluene-4-sulfonic acid (104-15-4) + 4-[2-(2-amino-4,7-dihydro-4-oxo-1H-pyrrolo[2,3-d]pyrimidin-5-yl )ethyl]benzoic acid (137281-39-1) → N-[4-[2-(2-amino-4,7-dihydro-4-oxo-1H-pyrrolo[2,3-d]-pyrimidin-5-yl)ethyl]benzoyl]-L-glutamic acid diethyl ester 4-methylbenzenesulfonic acid salt (165049-28-5)

Guidance literature:

diethyl-L-glutamate hydrochloride; 4-[2-(2-amino-4,7-dihydro-4-oxo-1H-pyrrolo[2,3-d]pyrimidin-5-yl )ethyl]benzoic acid; With 4-methyl-morpholine; 2-chloro-4,6-dimethoxy-1 ,3,5-triazine; In N,N-dimethyl-formamide; at 20 ℃; for 3h; Inert atmosphere; Industrial scale;

toluene-4-sulfonic acid; In ethanol; N,N-dimethyl-formamide; at 70 ℃; Temperature; Inert atmosphere; Industrial scale;

Reference yield:

toluene-4-sulfonic acid (104-15-4) → pemetrexed diethyl ester p-toluenesulfonic acid salt (165049-28-5)

Guidance literature:

4-(2-(2-amino-4-oxo-4,7-dihydro-1H-pyrrolo[2,3-d]pyrimidin-5-yl)ethyl)benzoic acid; With 4-methyl-morpholine; 2-chloro-4,6-dimethoxy-1 ,3,5-triazine; In N,N-dimethyl-formamide; at 5 ℃; for 1h;

diethyl-L-glutamate hydrochloride; In N,N-dimethyl-formamide; at 20 ℃; for 1h;

toluene-4-sulfonic acid; In ethanol; at 75 ℃; for 1h; Heating / reflux;

upstream raw materials:

toluene-4-sulfonic acid

diethyl-L-glutamate hydrochloride

4-(4-carbomethoxyphenyl)butanal

4-(3-bromo-4-oxobutyl)benzoic acid methyl ester

Downstream raw materials:

pemetrexed

(2S)-2-[[4-[2-(2-amino-1-methyl-4-oxo-4,7-dihydro-1H-pyrrolo[2,3-d]pyrimidin-5-yl)ethyl]benzoyl]amino]pentanedioic acid

Refernces

• 1、 -. "Pemetrexed disodium intermediate and preparation method thereof". Paragraph 0097-0100. . Retrieved 2019/10/17.
• 2、 -. "Pemetrexed disodium intermediate and preparation method thereof". Paragraph 0085-0088. . Retrieved 2019/10/17.