N~6~-[(benzyloxy)carbonyl]-N~2~-(4-{[(2,4-diaminopteridin-6-yl)methyl](methyl)amino}benzoyl)lysine

Base Information

• Chemical Name: N~6~-[(benzyloxy)carbonyl]-N~2~-(4-{[(2,4-diaminopteridin-6-yl)methyl](methyl)amino}benzoyl)lysine
• CAS No.: 51865-82-8
• Molecular Formula: C29H33N9O5
• Molecular Weight: 587.6296
• Mol file: 51865-82-8.mol

Synonyms:

Chemical Property of N~6~-[(benzyloxy)carbonyl]-N~2~-(4-{[(2,4-diaminopteridin-6-yl)methyl](methyl)amino}benzoyl)lysine

Chemical Property:

• Boiling Point: °Cat760mmHg
• Flash Point: °C
• Density: 1.387g/cm³

Purity/Quality:

99%min ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of N~6~-[(benzyloxy)carbonyl]-N~2~-(4-{[(2,4-diaminopteridin-6-yl)methyl](methyl)amino}benzoyl)lysine

There total 7 articles about N~6~-[(benzyloxy)carbonyl]-N~2~-(4-{[(2,4-diaminopteridin-6-yl)methyl](methyl)amino}benzoyl)lysine 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: 84.0%

Nα-(4-amino-4-deoxy-N10-methylpteroyl)-Nε-carbobenzoxy-L-lysine methyl ester (56892-79-6) → Nα-(4-amino-4-deoxy-N10-methylpteroyl)-Nε-carbobenzoxy-L-lysine (51865-82-8)

Guidance literature:

With piperidine; at 0 - 10 ℃; for 1.5h;

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)-Nε-carbobenzoxy-L-lysine (51865-82-8)

Guidance literature:

Multi-step reaction with 3 steps

1: N-methylmorpholine / various solvent(s) / 0.33 h / 0 °C

2: N-methylmorpholine / 1 h / 60 °C

3: 67 percent / 70percent aq. trifluoroacetic acid / 6 h / Ambient temperature

With 4-methyl-morpholine; trifluoroacetic acid; In various solvent(s);

DOI:10.1021/jm00346a026

Reference yield:

C19H24N7O5P → Nα-(4-amino-4-deoxy-N10-methylpteroyl)-Nε-carbobenzoxy-L-lysine (51865-82-8)

Guidance literature:

Multi-step reaction with 2 steps

1: Et₃N / dimethylformamide / 72 h / Ambient temperature

2: 84 percent / aq. piperidine / 1.5 h / 0 - 10 °C

With piperidine; triethylamine; In N,N-dimethyl-formamide;

DOI:10.1021/jm00350a015

upstream raw materials:

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

4-[(2,4-diamino-pteridin-6-ylmethyl)-methyl-amino]-benzoic O-isobutyl-carbonic anhydride

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

N(ε)-benzoyloxycarbonyl-L-lysine tert-butyl ester hydrochloride

Downstream raw materials:

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

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

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.