(6R,9S)-1-aza-4-benzyl-3-<amino>-9-carboxy-2-oxobicyclo<4.3.0>non-3-ene

Base Information

• Chemical Name: (6R,9S)-1-aza-4-benzyl-3-<amino>-9-carboxy-2-oxobicyclo<4.3.0>non-3-ene
• CAS No.: 173395-78-3
• Molecular Formula: C₂₇H₂₉N₃O₆
• Molecular Weight: 491.544
• Mol file: 173395-78-3.mol

Synonyms:(6R,9S)-1-aza-4-benzyl-3-<amino>-9-carboxy-2-oxobicyclo<4.3.0>non-3-ene

Chemical Property of (6R,9S)-1-aza-4-benzyl-3-<amino>-9-carboxy-2-oxobicyclo<4.3.0>non-3-ene

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (6R,9S)-1-aza-4-benzyl-3-<amino>-9-carboxy-2-oxobicyclo<4.3.0>non-3-ene

There total 11 articles about (6R,9S)-1-aza-4-benzyl-3-<amino>-9-carboxy-2-oxobicyclo<4.3.0>non-3-ene 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: 72.0%

(6R,9S)-1-aza-4-benzyl-3-<amino>-9-(hydroxymethyl)-2-oxobicyclo<4.3.0>non-3-ene (173395-77-2) → (6R,9S)-1-aza-4-benzyl-3-<amino>-9-carboxy-2-oxobicyclo<4.3.0>non-3-ene (173395-78-3)

Guidance literature:

With jones reagent; In acetone; 1.) 0 deg C, 0.5 h, 2.) room temperature, 1.5 h;

DOI:10.1021/jo00130a015

Reference yield:

(2S)-2-<(benzyloxy)methyl>-5-methoxy-1-(3-phenyl-4-pentenoyl)pyrrolidine → (6R,9S)-1-aza-4-benzyl-3-<amino>-9-carboxy-2-oxobicyclo<4.3.0>non-3-ene (173395-78-3)

Guidance literature:

Multi-step reaction with 8 steps

1: 90 percent / TiCl₄ / CH₂Cl₂ / Ambient temperature

2: 78 percent / H₂, NaOMe / 5percent Pd/C / methanol

3: 90 percent / DBU / CH₂Cl₂ / 1 h / Ambient temperature

4: 63 percent / n-BuLi, diisopropylamine, O₂ / tetrahydrofuran; hexane / 0.5 h / -78 °C

5: 45 percent / NH₃ / methanol / 1.) 0 deg C, 2.) room temperature, 3 d

6: 67 percent / HOBt, EDCI / CH₂Cl₂ / 1.) 0 deg C, 5 min, 2.) room temperature, overnight

7: 91 percent / 2 N H₂SO₄ / tetrahydrofuran / Ambient temperature

8: 72 percent / Jones reagent / acetone / 1.) 0 deg C, 0.5 h, 2.) room temperature, 1.5 h

With n-butyllithium; jones reagent; sulfuric acid; ammonia; hydrogen; oxygen; sodium methylate; titanium tetrachloride; benzotriazol-1-ol; 1,8-diazabicyclo[5.4.0]undec-7-ene; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; diisopropylamine; palladium on activated charcoal; In tetrahydrofuran; methanol; hexane; dichloromethane; acetone;

DOI:10.1021/jo00130a015

Reference yield:

(9S)-1-aza-4-(chlorobenzyl)-9-(hydroxymethyl)-2-oxobicyclo<4.3.0>nonane → (6R,9S)-1-aza-4-benzyl-3-<amino>-9-carboxy-2-oxobicyclo<4.3.0>non-3-ene (173395-78-3)

Guidance literature:

Multi-step reaction with 7 steps

1: 78 percent / H₂, NaOMe / 5percent Pd/C / methanol

2: 90 percent / DBU / CH₂Cl₂ / 1 h / Ambient temperature

3: 63 percent / n-BuLi, diisopropylamine, O₂ / tetrahydrofuran; hexane / 0.5 h / -78 °C

4: 45 percent / NH₃ / methanol / 1.) 0 deg C, 2.) room temperature, 3 d

5: 67 percent / HOBt, EDCI / CH₂Cl₂ / 1.) 0 deg C, 5 min, 2.) room temperature, overnight

6: 91 percent / 2 N H₂SO₄ / tetrahydrofuran / Ambient temperature

7: 72 percent / Jones reagent / acetone / 1.) 0 deg C, 0.5 h, 2.) room temperature, 1.5 h

With n-butyllithium; jones reagent; sulfuric acid; ammonia; hydrogen; oxygen; sodium methylate; benzotriazol-1-ol; 1,8-diazabicyclo[5.4.0]undec-7-ene; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; diisopropylamine; palladium on activated charcoal; In tetrahydrofuran; methanol; hexane; dichloromethane; acetone;

DOI:10.1021/jo00130a015

upstream raw materials:

(6R,9S)-1-aza-4-benzyl-3-<amino>-9-(hydroxymethyl)-2-oxobicyclo<4.3.0>non-3-ene

(6R,9S)-1-aza-3-amino-4-benzyl-9-<(tert-butyldimethylsiloxy)methyl>-2-oxobicyclo<4.3.0>non-3-ene

(6R,9S)-1-aza-4-benzyl-9-<(tert-butyldimethylsiloxy)methyl>-3-<amino>-2-oxobicyclo<4.3.0>non-3-ene

(S)-1-Pyrrolidin-2-yl-methanol