ethyl N^α-[4-[3-(2,4-diamino-7H-pyrrolo[2,3-d]pyrimidin-5-yl)propyl]benzoyl]-N^δ-benzyoxycarbonyl-L-ornithinate

Base Information

• Chemical Name: ethyl N^α-[4-[3-(2,4-diamino-7H-pyrrolo[2,3-d]pyrimidin-5-yl)propyl]benzoyl]-N^δ-benzyoxycarbonyl-L-ornithinate
• CAS No.: 303957-90-6
• Molecular Formula: C₃₁H₃₇N₇O₅
• Molecular Weight: 587.679

Synonyms:ethyl N^α-[4-[3-(2,4-diamino-7H-pyrrolo[2,3-d]pyrimidin-5-yl)propyl]benzoyl]-N^δ-benzyoxycarbonyl-L-ornithinate

Chemical Property of ethyl N^α-[4-[3-(2,4-diamino-7H-pyrrolo[2,3-d]pyrimidin-5-yl)propyl]benzoyl]-N^δ-benzyoxycarbonyl-L-ornithinate

Chemical Property:

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Technology Process of ethyl N^α-[4-[3-(2,4-diamino-7H-pyrrolo[2,3-d]pyrimidin-5-yl)propyl]benzoyl]-N^δ-benzyoxycarbonyl-L-ornithinate

There total 1 articles about ethyl N^α-[4-[3-(2,4-diamino-7H-pyrrolo[2,3-d]pyrimidin-5-yl)propyl]benzoyl]-N^δ-benzyoxycarbonyl-L-ornithinate 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: 76.0%

4-<2-(2,4-diamino-7H-pyrrolo<2,3-d>pyrimidin-5-yl)propyl>benzoic acid (134373-15-2) + ethyl Nδ-benzyloxycarbonyl-L-ornithinate (54229-79-7) → ethyl Nα-[4-[3-(2,4-diamino-7H-pyrrolo[2,3-d]pyrimidin-5-yl)propyl]benzoyl]-Nδ-benzyoxycarbonyl-L-ornithinate (303957-90-6)

Guidance literature:

With triethylamine; diethyl dicarbonate; In N,N-dimethyl-formamide; at 20 ℃; for 4h;

DOI:10.1248/cpb.48.1270

Reference yield:

ethyl Nα-[4-[3-(2,4-diamino-7H-pyrrolo[2,3-d]pyrimidin-5-yl)propyl]benzoyl]-Nδ-benzyoxycarbonyl-L-ornithinate (303957-90-6) → Nα-[4-[3-(2,4-diamino-7H-pyrrolo[2,3-d]pyrimidin-5-yl)propyl]benzoyl]-Nε-benzyoxycarbonyl-L-ornithine (303957-81-5)

Guidance literature:

With sodium hydroxide; In tetrahydrofuran; methanol; at 20 ℃; for 3h;

DOI:10.1248/cpb.48.1270

Reference yield:

ethyl Nα-[4-[3-(2,4-diamino-7H-pyrrolo[2,3-d]pyrimidin-5-yl)propyl]benzoyl]-Nδ-benzyoxycarbonyl-L-ornithinate (303957-90-6) → 5-amino-2-{4-[3-(2,4-diamino-7H-pyrrolo[2,3-d]pyrimidin-5-yl)-propyl]-benzoylamino}-pentanoic acid

Guidance literature:

Multi-step reaction with 2 steps

1: 1N aq. NaOH / methanol; tetrahydrofuran / 3 h / 20 °C

2: H₂; 0.1 N aq. NaOH / 10 percent Pd/C / methanol; tetrahydrofuran / 12 h

With sodium hydroxide; hydrogen; palladium on activated charcoal; In tetrahydrofuran; methanol;

DOI:10.1248/cpb.48.1270

upstream raw materials:

4-<2-(2,4-diamino-7H-pyrrolo<2,3-d>pyrimidin-5-yl)propyl>benzoic acid

ethyl N^δ-benzyloxycarbonyl-L-ornithinate

Downstream raw materials:

N^α-[4-[3-(2,4-diamino-7H-pyrrolo[2,3-d]pyrimidin-5-yl)propyl]benzoyl]-N^ε-benzyoxycarbonyl-L-ornithine

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