ornithine-methotrexate

Base Information

• Chemical Name: ornithine-methotrexate
• CAS No.: 80407-73-4
• Molecular Formula: C20H25 N9 O3
• Molecular Weight: 439.47
• Mol file: 80407-73-4.mol

Synonyms:ornithine-methotrexate

Chemical Property of ornithine-methotrexate

Chemical Property:

• PSA: 199.26000
• Density: 1.442g/cm³
• LogP: 2.39610

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of ornithine-methotrexate

There total 8 articles about ornithine-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: 64.0%

Nα-(4-amino-4-deoxy-N10-methylpteroyl)-Nδ-carbobenzoxy-L-ornithine (80407-74-5) → Nα-(4-amino-4-deoxy-N10-methylpteroyl)-L-ornithine (80407-73-4)

Guidance literature:

With tris(trifluoro acetyloxy)borane; In trifluoroacetic acid; at 0 ℃; for 7h;

DOI:10.1021/jm00346a026

Reference yield:

4-[(2,4-diaminopteridin-6-ylmethyl)methylamino]benzoic acid (19741-14-1) → Nα-(4-amino-4-deoxy-N10-methylpteroyl)-L-ornithine (80407-73-4)

Guidance literature:

Multi-step reaction with 3 steps

1: 86 percent / Et₃N / dimethylformamide / 5 h / 55 °C

2: Et₃N / dimethylformamide / 72 h / 55 °C

3: 80 percent / trifluoroacetic acid / 3 h

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

DOI:10.1021/jm00155a012

Reference yield:

p-nitrophenyl 4-amino-4-deoxy-N10-formylpteroate (95485-01-1) → Nα-(4-amino-4-deoxy-N10-methylpteroyl)-L-ornithine (80407-73-4)

Guidance literature:

Multi-step reaction with 2 steps

1: Et₃N / dimethylformamide / 72 h / 55 °C

2: 80 percent / trifluoroacetic acid / 3 h

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

DOI:10.1021/jm00155a012

upstream raw materials:

N^α-(4-amino-4-deoxy-N¹⁰-methylpteroyl)-N^δ-carbobenzoxy-L-ornithine

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

N^δ-(tert-butoxycarbonyl)-L-ornithine

p-nitrophenyl 4-amino-4-deoxy-N¹⁰-formylpteroate

Downstream raw materials:

Sodium; (S)-5-(2-bromo-acetylamino)-2-{4-[(2,4-diamino-pteridin-6-ylmethyl)-methyl-amino]-benzoylamino}-pentanoate

Sodium; (S)-5-(2-chloro-acetylamino)-2-{4-[(2,4-diamino-pteridin-6-ylmethyl)-methyl-amino]-benzoylamino}-pentanoate

Refernces

• 1、 Kempton, Robert J.,Black, Angelique M.,Anstead, Gregory M.,Kumar, A. Ashok,Blankenship, Dale T.,Freisheim, James H.. "Lysine and Ornithine Analogues of Methotrexate as Inhibitors of Dihydrofolate Reductase". . p. 475 - 477. Retrieved 2007/10/02.