methyl 11-((S)-2-((3S,6S,7R,9aS)-7-(2-benzamidoethyl)-6-((R)-2-((tert-butoxycarbonyl)(methyl)amino)butanamido)-5-oxooctahydro-1H-pyrrolo[1,2-a]azepine-3-carboxamido)-2-phenylacetamido)undecanoate

Base Information

• Chemical Name: methyl 11-((S)-2-((3S,6S,7R,9aS)-7-(2-benzamidoethyl)-6-((R)-2-((tert-butoxycarbonyl)(methyl)amino)butanamido)-5-oxooctahydro-1H-pyrrolo[1,2-a]azepine-3-carboxamido)-2-phenylacetamido)undecanoate
• CAS No.: 1608150-83-9
• Molecular Formula: C₄₉H₇₂N₆O₉
• Molecular Weight: 889.145
• Mol file: 1608150-83-9.mol

Synonyms:methyl 11-((S)-2-((3S,6S,7R,9aS)-7-(2-benzamidoethyl)-6-((R)-2-((tert-butoxycarbonyl)(methyl)amino)butanamido)-5-oxooctahydro-1H-pyrrolo[1,2-a]azepine-3-carboxamido)-2-phenylacetamido)undecanoate

Chemical Property of methyl 11-((S)-2-((3S,6S,7R,9aS)-7-(2-benzamidoethyl)-6-((R)-2-((tert-butoxycarbonyl)(methyl)amino)butanamido)-5-oxooctahydro-1H-pyrrolo[1,2-a]azepine-3-carboxamido)-2-phenylacetamido)undecanoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl 11-((S)-2-((3S,6S,7R,9aS)-7-(2-benzamidoethyl)-6-((R)-2-((tert-butoxycarbonyl)(methyl)amino)butanamido)-5-oxooctahydro-1H-pyrrolo[1,2-a]azepine-3-carboxamido)-2-phenylacetamido)undecanoate

There total 13 articles about methyl 11-((S)-2-((3S,6S,7R,9aS)-7-(2-benzamidoethyl)-6-((R)-2-((tert-butoxycarbonyl)(methyl)amino)butanamido)-5-oxooctahydro-1H-pyrrolo[1,2-a]azepine-3-carboxamido)-2-phenylacetamido)undecanoate 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: 61.0%

(3S,6S,7R,9aS)-7-(2-benzamidoethyl)-6-((R)-2-((tert-butoxycarbonyl)(methyl)amino)butanamido)-5-oxooctahydro-1H-pyrrolo-[1,2-a]azepine-3-carboxylic acid (1608150-75-9) + (S)-methyl 11-((2-amino)-2-phenylacetamido)undecanoate hydrochloride (1608150-82-8) → methyl 11-((S)-2-((3S,6S,7R,9aS)-7-(2-benzamidoethyl)-6-((R)-2-((tert-butoxycarbonyl)(methyl)amino)butanamido)-5-oxooctahydro-1H-pyrrolo[1,2-a]azepine-3-carboxamido)-2-phenylacetamido)undecanoate (1608150-83-9)

Guidance literature:

(3S,6S,7R,9aS)-7-(2-benzamidoethyl)-6-((R)-2-((tert-butoxycarbonyl)(methyl)amino)butanamido)-5-oxooctahydro-1H-pyrrolo-[1,2-a]azepine-3-carboxylic acid; With 1-hydroxy-7-aza-benzotriazole; N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; In N,N-dimethyl-formamide; at 20 ℃; for 0.166667h; Inert atmosphere;

(S)-methyl 11-((2-amino)-2-phenylacetamido)undecanoate hydrochloride; In N,N-dimethyl-formamide; at 20 ℃; for 43h; Inert atmosphere;

DOI:10.1039/c4ob00207e

Reference yield:

(3S,6S,7R,9aS)-methyl 6-((tert-butoxycarbonyl)amino)-7-(cyanomethyl)-5-oxooctahydro-1H-pyrrolo[1,2-a]azepine-3-carboxylate (1412423-66-5) → methyl 11-((S)-2-((3S,6S,7R,9aS)-7-(2-benzamidoethyl)-6-((R)-2-((tert-butoxycarbonyl)(methyl)amino)butanamido)-5-oxooctahydro-1H-pyrrolo[1,2-a]azepine-3-carboxamido)-2-phenylacetamido)undecanoate (1608150-83-9)

Guidance literature:

Multi-step reaction with 6 steps

1.1: acetyl chloride; methanol / 0.08 h / 20 °C / Inert atmosphere

2.1: N-ethyl-N,N-diisopropylamine; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol / dichloromethane / 0.17 h / Inert atmosphere

2.2: 22 h / 20 °C / Inert atmosphere

3.1: hydrogen; citric acid / water; ethanol / 29 h / 60 °C / 45004.5 Torr / Flow reactor

4.1: triethylamine / dichloromethane / 5 h / 20 °C / Inert atmosphere

5.1: lithium hydroxide; water / tetrahydrofuran / 5.5 h / 0 - 20 °C

6.1: N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; 1-hydroxy-7-aza-benzotriazole / N,N-dimethyl-formamide / 0.17 h / 20 °C / Inert atmosphere

6.2: 43 h / 20 °C / Inert atmosphere

With methanol; 1-hydroxy-7-aza-benzotriazole; water; hydrogen; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; N-ethyl-N,N-diisopropylamine; acetyl chloride; citric acid; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; lithium hydroxide; In tetrahydrofuran; ethanol; dichloromethane; water; N,N-dimethyl-formamide;

DOI:10.1039/c4ob00207e

Reference yield:

(3S,6S,7S,9aS)-methyl 6-(tert-butoxycarbonylamino)-7-(hydroxymethyl)-5-oxooctahydro-1H-pyrrolo[1,2-a]azepine-3-carboxylate → methyl 11-((S)-2-((3S,6S,7R,9aS)-7-(2-benzamidoethyl)-6-((R)-2-((tert-butoxycarbonyl)(methyl)amino)butanamido)-5-oxooctahydro-1H-pyrrolo[1,2-a]azepine-3-carboxamido)-2-phenylacetamido)undecanoate (1608150-83-9)

Guidance literature:

Multi-step reaction with 8 steps

1.1: triethylamine / dichloromethane / 2 h / 0 - 20 °C / Inert atmosphere

2.1: N,N-dimethyl-formamide / 2 h / 80 °C / Microwave irradiation

3.1: acetyl chloride; methanol / 0.08 h / 20 °C / Inert atmosphere

4.1: N-ethyl-N,N-diisopropylamine; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol / dichloromethane / 0.17 h / Inert atmosphere

4.2: 22 h / 20 °C / Inert atmosphere

5.1: hydrogen; citric acid / water; ethanol / 29 h / 60 °C / 45004.5 Torr / Flow reactor

6.1: triethylamine / dichloromethane / 5 h / 20 °C / Inert atmosphere

7.1: lithium hydroxide; water / tetrahydrofuran / 5.5 h / 0 - 20 °C

8.1: N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; 1-hydroxy-7-aza-benzotriazole / N,N-dimethyl-formamide / 0.17 h / 20 °C / Inert atmosphere

8.2: 43 h / 20 °C / Inert atmosphere

With methanol; 1-hydroxy-7-aza-benzotriazole; water; hydrogen; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; N-ethyl-N,N-diisopropylamine; acetyl chloride; citric acid; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; lithium hydroxide; In tetrahydrofuran; ethanol; dichloromethane; water; N,N-dimethyl-formamide;

DOI:10.1039/c4ob00207e

upstream raw materials:

C₁₂H₂₀N₂O₄

C₁₉H₂₄N₂O₄

(3S,6S,7R,9aS)-methyl 6-((tert-butoxycarbonyl)amino)-7-(cyanomethyl)-5-oxooctahydro-1H-pyrrolo[1,2-a]azepine-3-carboxylate

(3S,6S,7R,9aS)-methyl 6-((R)-2-((tert-butoxycarbonyl)(methyl)amino)butanamido)-7-(cyanomethyl)-5-oxooctahydro-1H-pyrrolo[1,2-a]azepine-3-carboxylate

Downstream raw materials:

11-((S)-2-((3S,6S,7R,9aS)-7-(2-benzamidoethyl)-6-((R)-2-((tertbutoxycarbonyl)(methyl)amino)butanamido)-5-oxooctahydro-1H-pyrrolo[1,2-a]azepine-3-carboxamido)-2-phenylacetamido)undecanoic acid

methyl 11-((S)-2-((3S,6S,7R,9aS)-7-(2-benzamidoethyl)-6-((S)-2-(methylamino)butanamido)-5-oxooctahydro-1H-pyrrolo[1,2-a]azepine-3-carboxamido)-2-phenylacetamido)undecanoate hydrochloride

Refernces