N²-<4-<<(2,4-diamino-6-pteridinyl)methyl>methylamino>benzoyl>-N⁵-<(1,1-dimethylethoxy)carbonyl>-2,5-diaminopentanoic acid

Base Information

• Chemical Name: N²-<4-<<(2,4-diamino-6-pteridinyl)methyl>methylamino>benzoyl>-N⁵-<(1,1-dimethylethoxy)carbonyl>-2,5-diaminopentanoic acid
• CAS No.: 96846-16-1
• Molecular Formula: C₂₅H₃₃N₉O₅
• Molecular Weight: 539.594

Synonyms:N²-<4-<<(2,4-diamino-6-pteridinyl)methyl>methylamino>benzoyl>-N⁵-<(1,1-dimethylethoxy)carbonyl>-2,5-diaminopentanoic acid

Chemical Property of N²-<4-<<(2,4-diamino-6-pteridinyl)methyl>methylamino>benzoyl>-N⁵-<(1,1-dimethylethoxy)carbonyl>-2,5-diaminopentanoic acid

Chemical Property:

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Technology Process of N²-<4-<<(2,4-diamino-6-pteridinyl)methyl>methylamino>benzoyl>-N⁵-<(1,1-dimethylethoxy)carbonyl>-2,5-diaminopentanoic acid

There total 7 articles about N²-<4-<<(2,4-diamino-6-pteridinyl)methyl>methylamino>benzoyl>-N⁵-<(1,1-dimethylethoxy)carbonyl>-2,5-diaminopentanoic 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: 95.0%

6-bromomethyl-2,4-diaminopteridine hydrobromide (52853-40-4) + N2-<4-(methylamino)benzoyl>-Nω-<(1,1-dimethylethoxy)carbonyl>-2,ω-diaminopentanoic acid (96845-99-7) → N2-<4-<<(2,4-diamino-6-pteridinyl)methyl>methylamino>benzoyl>-N5-<(1,1-dimethylethoxy)carbonyl>-2,5-diaminopentanoic acid (96846-16-1)

Guidance literature:

In N,N-dimethyl acetamide; at 20 - 25 ℃; for 120h;

DOI:10.1021/jm00146a008

Reference yield:

Z-Orn(Boc)-OH (7733-29-1,199924-46-4) → N2-<4-<<(2,4-diamino-6-pteridinyl)methyl>methylamino>benzoyl>-N5-<(1,1-dimethylethoxy)carbonyl>-2,5-diaminopentanoic acid (96846-16-1)

Guidance literature:

Multi-step reaction with 4 steps

1: H₂ / 5percent Pd/C / methanol; H₂O / 7 h / 25 °C / 2327.2 - 2585.7 Torr

2: 85 percent / (i-Pr)2NEt / dioxane; H₂O / Ambient temperature

3: 100 percent / H₂ / 5percent Pd/C / dioxane / 25 °C / 2316.8 - 2589 Torr

4: 95 percent / N,N-dimethyl-acetamide / 120 h / 20 - 25 °C

With hydrogen; N-ethyl-N,N-diisopropylamine; palladium on activated charcoal; In 1,4-dioxane; methanol; N,N-dimethyl acetamide; water;

DOI:10.1021/jm00146a008

Reference yield:

Nδ-(tert-butoxycarbonyl)-L-ornithine (13650-49-2,184576-63-4) → N2-<4-<<(2,4-diamino-6-pteridinyl)methyl>methylamino>benzoyl>-N5-<(1,1-dimethylethoxy)carbonyl>-2,5-diaminopentanoic acid (96846-16-1)

Guidance literature:

Multi-step reaction with 3 steps

1: 85 percent / (i-Pr)2NEt / dioxane; H₂O / Ambient temperature

2: 100 percent / H₂ / 5percent Pd/C / dioxane / 25 °C / 2316.8 - 2589 Torr

3: 95 percent / N,N-dimethyl-acetamide / 120 h / 20 - 25 °C

With hydrogen; N-ethyl-N,N-diisopropylamine; palladium on activated charcoal; In 1,4-dioxane; N,N-dimethyl acetamide; water;

DOI:10.1021/jm00146a008

upstream raw materials:

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

N^δ-(tert-butoxycarbonyl)-L-ornithine

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

6-bromomethyl-2,4-diaminopteridine hydrobromide

Downstream raw materials:

(S)-5-Amino-2-{4-[(2,4-diamino-pteridin-6-ylmethyl)-methyl-amino]-benzoylamino}-pentanoic acid; compound with trifluoro-acetic acid

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