(2R)-2-(4-cyclopropanesulfonyl-3-cyclopropylphenyl)-N-[5-(hydroxymethyl)pyrazin-2-yl]-3-[(R)-3-oxocyclopentyl]propanamide

Base Information

• Chemical Name: (2R)-2-(4-cyclopropanesulfonyl-3-cyclopropylphenyl)-N-[5-(hydroxymethyl)pyrazin-2-yl]-3-[(R)-3-oxocyclopentyl]propanamide
• CAS No.: 1174229-89-0
• Molecular Formula: C₂₅H₂₉N₃O₅S
• Molecular Weight: 483.588
• Mol file: 1174229-89-0.mol

Synonyms:(2R)-2-(4-cyclopropanesulfonyl-3-cyclopropylphenyl)-N-[5-(hydroxymethyl)pyrazin-2-yl]-3-[(R)-3-oxocyclopentyl]propanamide

Chemical Property of (2R)-2-(4-cyclopropanesulfonyl-3-cyclopropylphenyl)-N-[5-(hydroxymethyl)pyrazin-2-yl]-3-[(R)-3-oxocyclopentyl]propanamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R)-2-(4-cyclopropanesulfonyl-3-cyclopropylphenyl)-N-[5-(hydroxymethyl)pyrazin-2-yl]-3-[(R)-3-oxocyclopentyl]propanamide

There total 11 articles about (2R)-2-(4-cyclopropanesulfonyl-3-cyclopropylphenyl)-N-[5-(hydroxymethyl)pyrazin-2-yl]-3-[(R)-3-oxocyclopentyl]propanamide 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:

C31H43N3O5SSi (1174231-52-7) → (2R)-2-(4-cyclopropanesulfonyl-3-cyclopropylphenyl)-N-[5-(hydroxymethyl)pyrazin-2-yl]-3-[(R)-3-oxocyclopentyl]propanamide (1174229-89-0)

Guidance literature:

With hydrogenchloride; triphenylphosphine; In tetrahydrofuran; at 20 ℃; for 2h;

Reference yield:

methyl 5-chloropyrazine-2-carboxylate (33332-25-1) → (2R)-2-(4-cyclopropanesulfonyl-3-cyclopropylphenyl)-N-[5-(hydroxymethyl)pyrazin-2-yl]-3-[(R)-3-oxocyclopentyl]propanamide (1174229-89-0)

Guidance literature:

Multi-step reaction with 7 steps

1.1: sodium hydroxide / water / 20 °C / Inert atmosphere

2.1: oxalyl dichloride / N,N-dimethyl-formamide; 1,4-dioxane / 20 °C / Inert atmosphere

2.2: 5 °C / Inert atmosphere

3.1: 1H-imidazole / N,N-dimethyl-formamide / 2 h / 12 °C / Inert atmosphere; Industrial scale

4.1: tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; sodium t-butanolate / toluene / 70 °C / Inert atmosphere

5.1: Wilkinson's catalyst / acetonitrile; water / 100 °C / Inert atmosphere

6.1: N,N-dimethyl-formamide; dichloromethane / 3 h / -3 - -1 °C / Inert atmosphere; Industrial scale

7.1: hydrogenchloride / tetrahydrofuran; water / 3 h / 2 - 3 °C / Inert atmosphere; Industrial scale

With 1H-imidazole; hydrogenchloride; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; Wilkinson's catalyst; oxalyl dichloride; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; sodium hydroxide; sodium t-butanolate; In tetrahydrofuran; 1,4-dioxane; dichloromethane; water; N,N-dimethyl-formamide; toluene; acetonitrile;

DOI:10.1021/acs.oprd.6b00415

Reference yield:

(2R)-2-(4-cyclopropanesulfonyl-3-cyclopropylphenyl)-3-[(2R,3R,7R)-2,3-diphenyl-1,4-dioxaspiro[4.4]nonan-7-yl]propanoic acid → (2R)-2-(4-cyclopropanesulfonyl-3-cyclopropylphenyl)-N-[5-(hydroxymethyl)pyrazin-2-yl]-3-[(R)-3-oxocyclopentyl]propanamide (1174229-89-0)

Guidance literature:

Multi-step reaction with 4 steps

1: hydrogenchloride / water; acetone / 50 °C / Inert atmosphere; Industrial scale

2: dmap; pyridine; trichlorophosphate / N,N-dimethyl-formamide; dichloromethane / 1 h / -4 - -3 °C / Inert atmosphere; Industrial scale

3: N,N-dimethyl-formamide; dichloromethane / 3 h / -3 - -1 °C / Inert atmosphere; Industrial scale

4: hydrogenchloride / tetrahydrofuran; water / 3 h / 2 - 3 °C / Inert atmosphere; Industrial scale

With pyridine; hydrogenchloride; dmap; trichlorophosphate; In tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide; acetone;

DOI:10.1021/acs.oprd.6b00415

upstream raw materials:

C₃₁H₄₃N₃O₅SSi

methyl 2-[3-bromo-4-(cyclopropylsulfonyl)phenyl]-3-[(2R,3R,7R)-2,3-diphenyl-1,4-dioxaspiro[4.4]non-7-yl]propionate

methyl 5-chloropyrazine-2-carboxylate

2-[3-cyclopropyl-4-(cyclopropylsulfonyl)phenyl]-3-[(2R,3R,7R)-2,3-diphenyl-1,4-dioxaspiro[4.4]non-7-yl]propionic acid