(S)-methyl 2-((R)-1-(2-((S)-2-(1,3-dioxoisoindolin-2-yl)-3-methylbutanamido)benzoyl)pyrrolidine-2-carboxamido)-4-methylpentanoate

Base Information

• Chemical Name: (S)-methyl 2-((R)-1-(2-((S)-2-(1,3-dioxoisoindolin-2-yl)-3-methylbutanamido)benzoyl)pyrrolidine-2-carboxamido)-4-methylpentanoate
• CAS No.: 1539320-92-7
• Molecular Formula: C₃₂H₃₈N₄O₇
• Molecular Weight: 590.676
• Mol file: 1539320-92-7.mol

Synonyms:

Chemical Property of (S)-methyl 2-((R)-1-(2-((S)-2-(1,3-dioxoisoindolin-2-yl)-3-methylbutanamido)benzoyl)pyrrolidine-2-carboxamido)-4-methylpentanoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-methyl 2-((R)-1-(2-((S)-2-(1,3-dioxoisoindolin-2-yl)-3-methylbutanamido)benzoyl)pyrrolidine-2-carboxamido)-4-methylpentanoate

There total 7 articles about (S)-methyl 2-((R)-1-(2-((S)-2-(1,3-dioxoisoindolin-2-yl)-3-methylbutanamido)benzoyl)pyrrolidine-2-carboxamido)-4-methylpentanoate 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:

C19H27N3O4 (1539320-55-2) + N-phthalimide l-valinyl chloride (5511-73-9) → (S)-methyl 2-((R)-1-(2-((S)-2-(1,3-dioxoisoindolin-2-yl)-3-methylbutanamido)benzoyl)pyrrolidine-2-carboxamido)-4-methylpentanoate (1539320-92-7)

Guidance literature:

With triethylamine; In dichloromethane; at 20 ℃; for 1h;

DOI:10.1039/c3ob42016g

Reference yield:

N-(tert-butoxycarbonyl)-D-proline (37784-17-1,59433-50-0) → (S)-methyl 2-((R)-1-(2-((S)-2-(1,3-dioxoisoindolin-2-yl)-3-methylbutanamido)benzoyl)pyrrolidine-2-carboxamido)-4-methylpentanoate (1539320-92-7)

Guidance literature:

Multi-step reaction with 5 steps

1: dicyclohexyl-carbodiimide; dmap / dichloromethane / 12 h

2: trifluoroacetic acid / dichloromethane / 3 h / 20 °C

3: O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / dichloromethane / 12 h / 0 °C

4: trifluoroacetic acid / dichloromethane / 2 h

5: triethylamine / dichloromethane / 1 h / 20 °C

With dmap; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; triethylamine; N-ethyl-N,N-diisopropylamine; dicyclohexyl-carbodiimide; trifluoroacetic acid; In dichloromethane;

DOI:10.1039/c3ob42016g

Reference yield:

(S)-Leu-OMe (2666-93-5) → (S)-methyl 2-((R)-1-(2-((S)-2-(1,3-dioxoisoindolin-2-yl)-3-methylbutanamido)benzoyl)pyrrolidine-2-carboxamido)-4-methylpentanoate (1539320-92-7)

Guidance literature:

Multi-step reaction with 5 steps

1: dicyclohexyl-carbodiimide; dmap / dichloromethane / 12 h

2: trifluoroacetic acid / dichloromethane / 3 h / 20 °C

3: O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / dichloromethane / 12 h / 0 °C

4: trifluoroacetic acid / dichloromethane / 2 h

5: triethylamine / dichloromethane / 1 h / 20 °C

With dmap; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; triethylamine; N-ethyl-N,N-diisopropylamine; dicyclohexyl-carbodiimide; trifluoroacetic acid; In dichloromethane;

DOI:10.1039/c3ob42016g

upstream raw materials:

N-(tert-butoxycarbonyl)-D-proline

(S)-Leu-OMe

(R)-tert-butyl 2-(((S)-1-methoxy-4-methyl-1-oxopentan-2-yl)carbamoyl)pyrrolidine-1-carboxylate

(S)-methyl 2-((R)-1-(2-((tert-butoxycarbonyl)amino)benzoyl)-pyrrolidine-2-carboxamido)-4-methylpentanoate

Downstream raw materials:

(R)-N-((S)-4-methyl-1-(methylamino)-1-oxopentan-2-yl)-1-(2-((S)-3-methyl-2-pivalamidobutanamido)benzoyl)pyrrolidine-2-carboxamide