L-Glutamic acid, N-(4-(2-(2-amino-1,4-dihydro-4-oxopyrido(2,3-d)pyrimi din-6-yl)ethyl)bezoyl)-

Base Information

• Chemical Name: L-Glutamic acid, N-(4-(2-(2-amino-1,4-dihydro-4-oxopyrido(2,3-d)pyrimi din-6-yl)ethyl)bezoyl)-
• CAS No.: 85597-18-8
• Molecular Formula: C21H21 N5 O6
• Molecular Weight: 439.42134
• Mol file: 85597-18-8.mol

Synonyms:L-Glutamicacid, N-[4-[2-(2-amino-1,4-dihydro-4-oxopyrido[2,3-d]pyrimidin-6-yl)ethyl]benzoyl]-(9CI); Pyrido[2,3-d]pyrimidine, L-glutamic acid deriv.; 5,10-Dideazafolic acid

Chemical Property of L-Glutamic acid, N-(4-(2-(2-amino-1,4-dihydro-4-oxopyrido(2,3-d)pyrimi din-6-yl)ethyl)bezoyl)-

Chemical Property:

• PSA: 189.35000
• Density: 1.54g/cm³
• LogP: 1.46660

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of L-Glutamic acid, N-(4-(2-(2-amino-1,4-dihydro-4-oxopyrido(2,3-d)pyrimi din-6-yl)ethyl)bezoyl)-

There total 8 articles about L-Glutamic acid, N-(4-(2-(2-amino-1,4-dihydro-4-oxopyrido(2,3-d)pyrimi din-6-yl)ethyl)bezoyl)- 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: 86.0%

diethyl 2-acetyl-5,10-dideazafolate (95674-75-2) → 5,10-dideazafolic acid (85597-18-8)

Guidance literature:

With sodium hydroxide; In methanol; for 72h; Ambient temperature;

DOI:10.1021/jm00145a012

Reference yield:

diethyl N-(4-[2-(2-acetamido-4-hydroxypyrido[2,3-d]pyrimidin-6-yl)ethyl]benzoyl)-L-glutamate → 5,10-dideazafolic acid (85597-18-8)

Guidance literature:

With sodium hydroxide; acetic acid; In methanol;

Reference yield:

2,4-diamino-6-(4-carboxystyryl)-5-deazapteridine (95674-66-1) → 5,10-dideazafolic acid (85597-18-8)

Guidance literature:

Multi-step reaction with 6 steps

1: 88 percent / 1N NaOH / 3 h / Heating

2: 84 percent / 4-(dimethylamino)pyridine / 3 h / 120 °C

3: 77 percent / 1N NaOH / H₂O

4: 1.) N-methylpyrrolidone, N-methylmorpholine, phenyl N-phenylphosphoramidochloridate / 1.) 0 deg C, 30 min, 2.) RT, overnight

5: 56 percent / TFA, H₂ / 5percent Pd/C / 14 h / 2844.3 Torr / Ambient temperature

6: 86 percent / 1N NaOH / methanol / 72 h / Ambient temperature

With 4-methyl-morpholine; 1-methyl-pyrrolidin-2-one; dmap; sodium hydroxide; hydrogen; Phenyl N-phenylphosphoramidochloridate; trifluoroacetic acid; palladium on activated charcoal; In methanol; water;

DOI:10.1021/jm00145a012

upstream raw materials:

diethyl 2-acetyl-5,10-dideazafolate

4-<2-(2-amino-1,4-dihydro-4-oxopyrido<2,3-d>pyrimidin-6-yl)ethenyl>benzoic acid

2,4-diamino-6-(4-carboxystyryl)-5-deazapteridine

2-acetamide-6-(4-carboxystyryl)-5-deaza-4(3H)-pteridinone

Refernces

• 1、 Taylor, Edward C.,Harrington, Peter J.,Fletcher, Stephen R.,Beardsley, G. Peter,Moran, Richard, G.. "Synthesis of the Antileucemic Agents 5,10-Dideazaaminopterin and 5,10-Dideaza-5,6,7,8-tetrahydroaminopterin". . p. 914 - 921. Retrieved 2007/10/02.