N^α-(4-amino-4-deoxy-N¹⁰-methylpteroyl)-N^β-(tert-butyloxycarbonyl)-L-2,3-diaminopropionic acid

Base Information

• Chemical Name: N^α-(4-amino-4-deoxy-N¹⁰-methylpteroyl)-N^β-(tert-butyloxycarbonyl)-L-2,3-diaminopropionic acid
• CAS No.: 100484-54-6
• Molecular Formula: C₂₃H₂₉N₉O₅
• Molecular Weight: 511.541
• Mol file: 100484-54-6.mol

Synonyms:N^α-(4-amino-4-deoxy-N¹⁰-methylpteroyl)-N^β-(tert-butyloxycarbonyl)-L-2,3-diaminopropionic acid

Chemical Property of N^α-(4-amino-4-deoxy-N¹⁰-methylpteroyl)-N^β-(tert-butyloxycarbonyl)-L-2,3-diaminopropionic acid

Chemical Property:

Purity/Quality:

99% ，98% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N^α-(4-amino-4-deoxy-N¹⁰-methylpteroyl)-N^β-(tert-butyloxycarbonyl)-L-2,3-diaminopropionic acid

There total 10 articles about N^α-(4-amino-4-deoxy-N¹⁰-methylpteroyl)-N^β-(tert-butyloxycarbonyl)-L-2,3-diaminopropionic acid 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%

(S)-3-tert-Butoxycarbonylamino-2-{4-[(2,4-diamino-pteridin-6-ylmethyl)-methyl-amino]-benzoylamino}-propionic acid ethyl ester (96846-12-7) → Nα-(4-amino-4-deoxy-N10-methylpteroyl)-Nβ-(tert-butyloxycarbonyl)-L-2,3-diaminopropionic acid (100484-54-6)

Guidance literature:

With sodium hydroxide; In ethanol; at 20 - 25 ℃; for 4h;

DOI:10.1021/jm00146a008

Reference yield: 50.0%

p-nitrophenyl-4-amino-4-deoxy-N10-methylpteroate (57245-77-9) + (S)-2-amino-3-((tert-butoxycarbonyl)amino)propanoic acid (74536-29-1,259825-43-9) → Nα-(4-amino-4-deoxy-N10-methylpteroyl)-Nβ-(tert-butyloxycarbonyl)-L-2,3-diaminopropionic acid (100484-54-6)

Guidance literature:

With triethylamine; In N,N-dimethyl-formamide; at 55 ℃; for 72h;

DOI:10.1021/jm00155a012

Reference yield:

di-tert-butyl dicarbonate (24424-99-5) → Nα-(4-amino-4-deoxy-N10-methylpteroyl)-Nβ-(tert-butyloxycarbonyl)-L-2,3-diaminopropionic acid (100484-54-6)

Guidance literature:

Multi-step reaction with 6 steps

1: 77 percent / NaOH / H₂O; dioxane / 4.5 h

2: 1.) NH₃ (liq.), Na, 2.) (i-Pr)2NEt / 1.) -60 deg C, 10 min, 2.) H₂O, dioxane, 20-25 deg C, 17 h

3: 91 percent / (i-Pr)2NEt / dimethylformamide / 120 h / 20 - 25 °C

4: 97 percent / H₂ / 5percent Pd/C / dioxane / 760 Torr / Ambient temperature

5: 79 percent / N,N-dimethyl-acetamide / 144 h

6: 86 percent / NaOH / ethanol / 4 h / 20 - 25 °C

With sodium hydroxide; ammonia; hydrogen; sodium; N-ethyl-N,N-diisopropylamine; palladium on activated charcoal; In 1,4-dioxane; ethanol; N,N-dimethyl acetamide; water; N,N-dimethyl-formamide;

DOI:10.1021/jm00146a008

upstream raw materials:

p-nitrophenyl-4-amino-4-deoxy-N¹⁰-methylpteroate

(S)-2-amino-3-((tert-butoxycarbonyl)amino)propanoic acid

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

(S)-3-tert-Butoxycarbonylamino-2-{4-[(2,4-diamino-pteridin-6-ylmethyl)-methyl-amino]-benzoylamino}-propionic acid ethyl ester

Downstream raw materials:

(S)-3-Amino-2-{4-[(2,4-diamino-pteridin-6-ylmethyl)-methyl-amino]-benzoylamino}-propionic acid; compound with trifluoro-acetic acid

N^α-(4-amino-4-deoxy-N¹⁰-methylpteroyl)-L-2,3-diaminopropionic acid

Refernces

• 1、 Piper, J. R.,McCaleb, G. S.,Montgomery, J. A.,Schmid, F. A.,Sirotnak, F. M.. "Syntheses and Evaluation as Antifolates of MTX Analogues Derived from 2,ω-Diaminoalkanoic Acids". . p. 1016 - 1025. Retrieved 2007/10/02.