(1R,2S)-ethyl 1-((1R,2R,4R)-2-(hex-5-enyl(methyl)carbamoyl)-4-(7-methoxy-2-phenylquinazolin-4-yloxy)cyclopentanecarboxamido)-2-vinylcyclopropanecarboxylate

Base Information

• Chemical Name: (1R,2S)-ethyl 1-((1R,2R,4R)-2-(hex-5-enyl(methyl)carbamoyl)-4-(7-methoxy-2-phenylquinazolin-4-yloxy)cyclopentanecarboxamido)-2-vinylcyclopropanecarboxylate
• CAS No.: 923274-31-1
• Molecular Formula: C₃₇H₄₄N₄O₆
• Molecular Weight: 640.78
• Mol file: 923274-31-1.mol

Synonyms:(1R,2S)-ethyl 1-((1R,2R,4R)-2-(hex-5-enyl(methyl)carbamoyl)-4-(7-methoxy-2-phenylquinazolin-4-yloxy)cyclopentanecarboxamido)-2-vinylcyclopropanecarboxylate

Chemical Property of (1R,2S)-ethyl 1-((1R,2R,4R)-2-(hex-5-enyl(methyl)carbamoyl)-4-(7-methoxy-2-phenylquinazolin-4-yloxy)cyclopentanecarboxamido)-2-vinylcyclopropanecarboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1R,2S)-ethyl 1-((1R,2R,4R)-2-(hex-5-enyl(methyl)carbamoyl)-4-(7-methoxy-2-phenylquinazolin-4-yloxy)cyclopentanecarboxamido)-2-vinylcyclopropanecarboxylate

There total 13 articles about (1R,2S)-ethyl 1-((1R,2R,4R)-2-(hex-5-enyl(methyl)carbamoyl)-4-(7-methoxy-2-phenylquinazolin-4-yloxy)cyclopentanecarboxamido)-2-vinylcyclopropanecarboxylate 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: 85.0%

N-methylhex-5-en-1-amine hydrochloride (862175-17-5) + (1R,2R,4R)-2-((1R,2S)-1-ethoxycarbonyl-2-vinyl-cyclopropylcarbamoyl)-4-(7-methoxy-2-phenyl-quinazolin-4-yloxy)-cyclopentanecarboxylic acid (923274-30-0) → (1R,2S)-ethyl 1-((1R,2R,4R)-2-(hex-5-enyl(methyl)carbamoyl)-4-(7-methoxy-2-phenylquinazolin-4-yloxy)cyclopentanecarboxamido)-2-vinylcyclopropanecarboxylate (923274-31-1)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; HATU; In N,N-dimethyl-formamide; at 20 ℃;

Reference yield:

(1R,2R,4R)-2-((1R,2S)-1-ethoxycarbonyl-2-vinyl-cyclopropylcarbamoyl)-4-(7-methoxy-2-phenyl-quinazolin-4-yloxy)-cyclopentanecarboxylic acid (923274-30-0) + N-methylhex-5-en-1-amine (55863-02-0) → (1R,2S)-ethyl 1-((1R,2R,4R)-2-(hex-5-enyl(methyl)carbamoyl)-4-(7-methoxy-2-phenylquinazolin-4-yloxy)cyclopentanecarboxamido)-2-vinylcyclopropanecarboxylate (923274-31-1)

Guidance literature:

With 2-(1H-9-azabenzotriazol-1-yl)-1,1,3,3-tetramethyluroniumhexafluorophosphate; N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 0 - 20 ℃;

DOI:10.1016/j.bmcl.2010.05.029

Reference yield:

(1R,4R,5R)-3-oxo-2-oxabicyclo[2.2.1]heptane-5-carboxylic acid (862174-60-5) → (1R,2S)-ethyl 1-((1R,2R,4R)-2-(hex-5-enyl(methyl)carbamoyl)-4-(7-methoxy-2-phenylquinazolin-4-yloxy)cyclopentanecarboxamido)-2-vinylcyclopropanecarboxylate (923274-31-1)

Guidance literature:

Multi-step reaction with 6 steps

1: dmap / dichloromethane / 0 - 20 °C

2: lithium hydroxide; water / 1,4-dioxane / 0.75 h / 0 °C

3: N-ethyl-N,N-diisopropylamine; HATU / N,N-dimethyl-formamide / 2.5 h / 0 - 20 °C

4: di-isopropyl azodicarboxylate; triphenylphosphine / tetrahydrofuran / 12 h / 0 - 20 °C

5: triethylsilane; trifluorormethanesulfonic acid / dichloromethane / 2 h / 20 °C

6: N-ethyl-N,N-diisopropylamine; HATU / N,N-dimethyl-formamide / 20 °C

With triethylsilane; dmap; lithium hydroxide; trifluorormethanesulfonic acid; di-isopropyl azodicarboxylate; water; N-ethyl-N,N-diisopropylamine; triphenylphosphine; HATU; In tetrahydrofuran; 1,4-dioxane; dichloromethane; N,N-dimethyl-formamide; 4: Mitsunobu reaction;

upstream raw materials:

N-methylhex-5-en-1-amine hydrochloride

(1R,2R,4R)-2-((1R,2S)-1-ethoxycarbonyl-2-vinyl-cyclopropylcarbamoyl)-4-(7-methoxy-2-phenyl-quinazolin-4-yloxy)-cyclopentanecarboxylic acid

N-methylhex-5-en-1-amine

ethyl (1R,2S)-1-amino-2-vinylcyclopropanecarboxylate hydrochloride

Refernces

• 1、 -. "Macrocylic Inhibitors of Hepatitis C Virus". Page/Page column 38. . Retrieved 2009/05/28.