(2R,5S,8aS)-5-Benzyl-2-benzyloxy-hexahydro-3a,6,8-triaza-azulene-4,7-dione

Base Information

• Chemical Name: (2R,5S,8aS)-5-Benzyl-2-benzyloxy-hexahydro-3a,6,8-triaza-azulene-4,7-dione
• CAS No.: 913811-33-3
• Molecular Formula: C₂₁H₂₃N₃O₃
• Molecular Weight: 365.432

Synonyms:(2R,5S,8aS)-5-Benzyl-2-benzyloxy-hexahydro-3a,6,8-triaza-azulene-4,7-dione

Chemical Property of (2R,5S,8aS)-5-Benzyl-2-benzyloxy-hexahydro-3a,6,8-triaza-azulene-4,7-dione

Chemical Property:

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Technology Process of (2R,5S,8aS)-5-Benzyl-2-benzyloxy-hexahydro-3a,6,8-triaza-azulene-4,7-dione

There total 6 articles about (2R,5S,8aS)-5-Benzyl-2-benzyloxy-hexahydro-3a,6,8-triaza-azulene-4,7-dione 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: 99.0%

[(2S,4R)-1-((S)-2-Amino-3-phenyl-propionyl)-4-benzyloxy-pyrrolidin-2-yl]-carbamic acid 2,5-dioxo-pyrrolidin-1-yl ester; compound with trifluoro-acetic acid → (2R,5S,8aS)-5-Benzyl-2-benzyloxy-hexahydro-3a,6,8-triaza-azulene-4,7-dione (913811-33-3)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; In acetonitrile; at 20 ℃; for 0.5h;

DOI:10.1002/chem.200600560

Reference yield:

C26H31N3O5 → (2R,5S,8aS)-5-Benzyl-2-benzyloxy-hexahydro-3a,6,8-triaza-azulene-4,7-dione (913811-33-3)

Guidance literature:

C₂₆H₃₁N₃O₅; With 1-hydroxy-pyrrolidine-2,5-dione; In tetrahydrofuran; at 70 ℃; for 0.666667h;

With trifluoroacetic acid; In dichloromethane; at 20 ℃; for 0.166667h;

With N-ethyl-N,N-diisopropylamine; at 40 ℃; for 1h;

DOI:10.1002/chem.200600560

Reference yield:

C26H32N2O6 → (2R,5S,8aS)-5-Benzyl-2-benzyloxy-hexahydro-3a,6,8-triaza-azulene-4,7-dione (913811-33-3)

Guidance literature:

Multi-step reaction with 4 steps

1.1: N-methyl morpholine; ethyl chloroformate / tetrahydrofuran / 0.42 h / -20 °C

2.1: NaN₃ / tetrahydrofuran; H₂O / 0.08 h / 20 °C

3.1: toluene / 70 °C

4.1: (N-hydroxysuccinimide)polystyrene / tetrahydrofuran / 0.67 h / 70 °C

4.2: trifluoroacetic acid / CH₂Cl₂ / 0.17 h / 20 °C

4.3: diisopropylethylamine / 1 h / 40 °C

With 4-methyl-morpholine; 1-hydroxy-pyrrolidine-2,5-dione; sodium azide; chloroformic acid ethyl ester; In tetrahydrofuran; water; toluene; 3.1: Curtius rearrangement;

DOI:10.1002/chem.200600560

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