(2R)-2-(benzoylamino)-N-(N-cyclohexylphenylalanyl)-1,2,3,6-tetrahydro-6-oxocyclopenta[c]fluorene-2-carboxamide

Base Information

• Chemical Name: (2R)-2-(benzoylamino)-N-(N-cyclohexylphenylalanyl)-1,2,3,6-tetrahydro-6-oxocyclopenta[c]fluorene-2-carboxamide
• CAS No.: 1420468-17-2
• Molecular Formula: C₃₉H₃₇N₃O₄
• Molecular Weight: 611.74
• Mol file: 1420468-17-2.mol

Synonyms:

Chemical Property of (2R)-2-(benzoylamino)-N-(N-cyclohexylphenylalanyl)-1,2,3,6-tetrahydro-6-oxocyclopenta[c]fluorene-2-carboxamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R)-2-(benzoylamino)-N-(N-cyclohexylphenylalanyl)-1,2,3,6-tetrahydro-6-oxocyclopenta[c]fluorene-2-carboxamide

There total 12 articles about (2R)-2-(benzoylamino)-N-(N-cyclohexylphenylalanyl)-1,2,3,6-tetrahydro-6-oxocyclopenta[c]fluorene-2-carboxamide 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: 34.0%

2-(benzoylamino)-1,2,3,6-tetrahydro-6-oxocyclopenta[c]fluorene-2-carboxylic acid (1420468-13-8) + L-phenylalanine cyclohexylamide → (2S)-2-(benzoylamino)-N-(N-cyclohexylphenylalanyl)-1,2,3,6-tetrahydro-6-oxocyclopenta[c]fluorene-2-carboxamide (1420468-14-9) + (2R)-2-(benzoylamino)-N-(N-cyclohexylphenylalanyl)-1,2,3,6-tetrahydro-6-oxocyclopenta[c]fluorene-2-carboxamide (1420468-17-2)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; HATU; In tetrahydrofuran; at 20 ℃; for 120h; Cooling with ice;

DOI:10.1002/hlca.201200490

Reference yield:

6,7-dimethylisatin (20205-43-0) → (2R)-2-(benzoylamino)-N-(N-cyclohexylphenylalanyl)-1,2,3,6-tetrahydro-6-oxocyclopenta[c]fluorene-2-carboxamide (1420468-17-2)

Guidance literature:

Multi-step reaction with 11 steps

1.1: sodium hydroxide; dihydrogen peroxide / water / 0 °C

2.1: 1.25 h / 20 °C

3.1: diethyl ether; tetrahydrofuran / 3.5 h / -15 - 20 °C / Inert atmosphere

3.2: Cooling with ice

4.1: lithium hydroxide monohydrate / methanol; tetrahydrofuran; water / 48 h / 70 °C

5.1: hydrogenchloride; sodium nitrite / water / 4 h / 0 - 70 °C / Cooling with ice

6.1: tetrachloromethane; N-Bromosuccinimide; dibenzoyl peroxide / 2 h / Inert atmosphere; Reflux

7.1: 18-crown-6 ether; potassium carbonate / acetonitrile / 24 h / 20 °C / Inert atmosphere

8.1: hydrogenchloride / dichloromethane; water; ethanol / 4 h / 0 - 20 °C

9.1: acetonitrile / 18 h / 20 °C

10.1: sodium hydroxide / methanol; tetrahydrofuran; water / 1 h / 60 °C

11.1: HATU; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 120 h / 20 °C / Cooling with ice

With hydrogenchloride; tetrachloromethane; N-Bromosuccinimide; 18-crown-6 ether; lithium hydroxide monohydrate; dihydrogen peroxide; potassium carbonate; N-ethyl-N,N-diisopropylamine; HATU; sodium hydroxide; sodium nitrite; dibenzoyl peroxide; In tetrahydrofuran; methanol; diethyl ether; ethanol; dichloromethane; water; acetonitrile; 5.1: |Pschor Arylation;

DOI:10.1002/hlca.201200490

Reference yield:

2-amino-3,4-dimethylbenzoic acid (50419-58-4) → (2R)-2-(benzoylamino)-N-(N-cyclohexylphenylalanyl)-1,2,3,6-tetrahydro-6-oxocyclopenta[c]fluorene-2-carboxamide (1420468-17-2)

Guidance literature:

Multi-step reaction with 10 steps

1.1: 1.25 h / 20 °C

2.1: diethyl ether; tetrahydrofuran / 3.5 h / -15 - 20 °C / Inert atmosphere

2.2: Cooling with ice

3.1: lithium hydroxide monohydrate / methanol; tetrahydrofuran; water / 48 h / 70 °C

4.1: hydrogenchloride; sodium nitrite / water / 4 h / 0 - 70 °C / Cooling with ice

5.1: tetrachloromethane; N-Bromosuccinimide; dibenzoyl peroxide / 2 h / Inert atmosphere; Reflux

6.1: 18-crown-6 ether; potassium carbonate / acetonitrile / 24 h / 20 °C / Inert atmosphere

7.1: hydrogenchloride / dichloromethane; water; ethanol / 4 h / 0 - 20 °C

8.1: acetonitrile / 18 h / 20 °C

9.1: sodium hydroxide / methanol; tetrahydrofuran; water / 1 h / 60 °C

10.1: HATU; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 120 h / 20 °C / Cooling with ice

With hydrogenchloride; tetrachloromethane; N-Bromosuccinimide; 18-crown-6 ether; lithium hydroxide monohydrate; potassium carbonate; N-ethyl-N,N-diisopropylamine; HATU; sodium hydroxide; sodium nitrite; dibenzoyl peroxide; In tetrahydrofuran; methanol; diethyl ether; ethanol; dichloromethane; water; acetonitrile; 4.1: |Pschor Arylation;

DOI:10.1002/hlca.201200490

upstream raw materials:

ethyl 2-amino-1,2,3,6-tetrahydro-6-oxocyclopenta[c]fluorene-2-carboxylate

2-(benzoylamino)-1,2,3,6-tetrahydro-6-oxocyclopenta[c]fluorene-2-carboxylic acid

2,3-Dimethylaniline

6,7-dimethylisatin