lysine-methotrexate

Base Information

• Chemical Name: lysine-methotrexate
• CAS No.: 80407-56-3
• Molecular Formula: C21H27N9O3
• Molecular Weight: 453.4976
• Mol file: 80407-56-3.mol

Synonyms:(S)-6-Amino-2-{4-[(2,4-diamino-pteridin-6-ylmethyl)-methyl-amino]-benzoylamino}-hexanoic acid;

Chemical Property of lysine-methotrexate

Chemical Property:

• Boiling Point: °Cat760mmHg
• Flash Point: °C
• PSA: 199.26000
• Density: 1.411g/cm³
• LogP: 2.78620

Purity/Quality:

>95% ^*data from raw suppliers

Lysine-methotrexate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: Lysine-methotrexate is a derivative of Methotrexate (M260675), a folic acid antagonist.

Technology Process of lysine-methotrexate

There total 11 articles about lysine-methotrexate 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: 91.0%

Nα-(4-amino-4-deoxy-N10-methylpteroyl)-Nε-carbobenzoxy-L-lysine methyl ester (56892-79-6) → Nα-(4-amino-4-deoxy-N10-methylpteroyl)-L-lysine (80407-56-3,246224-40-8)

Guidance literature:

With hydrogen bromide; trifluoroacetic acid; for 0.0833333h; Heating;

DOI:10.1021/jm00350a015

Reference yield: 78.0%

Nα-(4-amino-4-deoxy-N10-methylpteroyl)-Nε-carbobenzoxy-L-lysine (51865-82-8) → Nα-(4-amino-4-deoxy-N10-methylpteroyl)-L-lysine (80407-56-3,246224-40-8)

Guidance literature:

With boron tribromide; trifluoroacetic acid; for 1h;

DOI:10.1021/jm00350a015

Reference yield:

4-[(2,4-diaminopteridin-6-ylmethyl)methylamino]benzoic acid (19741-14-1) → Nα-(4-amino-4-deoxy-N10-methylpteroyl)-L-lysine (80407-56-3,246224-40-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 56.1 percent / Et₃N, diethyl phosphorocyanidate (DEPC) / dimethylformamide / 20.5 h / 0 - 23 °C

2: 70percent aq. TFA / various solvent(s) / 4.5 h / Ambient temperature

With diethyl cyanophosphonate; triethylamine; trifluoroacetic acid; In N,N-dimethyl-formamide;

DOI:10.1021/jm00355a023

upstream raw materials:

N^α-(4-amino-4-deoxy-N¹⁰-methylpteroyl)-N^ε-carbobenzoxy-L-lysine methyl ester

N^α-(4-amino-4-deoxy-N¹⁰-methylpteroyl)-N^ε-carbobenzoxy-L-lysine

N^α-(4-amino-4-deoxy-N¹⁰-methylpteroyl)-N^ε-(tert-butoxycarbonyl)-L-lysine tert-butyl ester

4-[(2,4-diaminopteridin-6-ylmethyl)methylamino]benzoic acid

Downstream raw materials:

N^α-(4-amino-4-deoxy-N¹⁰-methylpteroyl)-N^ε-(iodoacetyl)-L-lysine

Sodium; (S)-6-(2-bromo-acetylamino)-2-{4-[(2,4-diamino-pteridin-6-ylmethyl)-methyl-amino]-benzoylamino}-hexanoate

Sodium; (S)-6-(2-chloro-acetylamino)-2-{4-[(2,4-diamino-pteridin-6-ylmethyl)-methyl-amino]-benzoylamino}-hexanoate

Refernces

• 1、 Rosowsky,Wright,Ginty,Uren. "Methotrexate analogues. 15. A methotrexate analogue designed for active-site-directed irreversible inactivation of dihydrofolate reductase". . p. 960 - 964. Retrieved 2007/10/02.
• 2、 Lee,Martinez,Goodman. "Folic acid antagonists. Methotrexate analogs containing spurious amino acids. Dichlorohomofolic acid". . p. 326 - 330. Retrieved 2007/10/06.