tert-butyl (2S)-2-[(isopropylamino)carbonyl]-4-[4-(methoxycarbonyl)-2-naphthyl]piperazine-1-carboxylate

Base Information

• Chemical Name: tert-butyl (2S)-2-[(isopropylamino)carbonyl]-4-[4-(methoxycarbonyl)-2-naphthyl]piperazine-1-carboxylate
• CAS No.: 954409-67-7
• Molecular Formula: C₂₅H₃₃N₃O₅
• Molecular Weight: 455.554

Synonyms:tert-butyl (2S)-2-[(isopropylamino)carbonyl]-4-[4-(methoxycarbonyl)-2-naphthyl]piperazine-1-carboxylate

Chemical Property of tert-butyl (2S)-2-[(isopropylamino)carbonyl]-4-[4-(methoxycarbonyl)-2-naphthyl]piperazine-1-carboxylate

Chemical Property:

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Technology Process of tert-butyl (2S)-2-[(isopropylamino)carbonyl]-4-[4-(methoxycarbonyl)-2-naphthyl]piperazine-1-carboxylate

There total 1 articles about tert-butyl (2S)-2-[(isopropylamino)carbonyl]-4-[4-(methoxycarbonyl)-2-naphthyl]piperazine-1-carboxylate 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:

3-nitro-1-naphthoic acid (4507-84-0) → tert-butyl (2S)-2-[(isopropylamino)carbonyl]-4-[4-(methoxycarbonyl)-2-naphthyl]piperazine-1-carboxylate (954409-67-7)

Guidance literature:

Multi-step reaction with 6 steps

1.1: oxalyl dichloride; N,N-dimethyl-formamide / dichloromethane / 3 h / 0 - 20 °C

2.1: dichloromethane / 1 h

3.1: hydrogen / palladium 10% on activated carbon / ethanol; dichloromethane / 3 h / 2068.65 Torr

4.1: hydrogen bromide; sodium nitrite / ethanol; water / 0.5 h / 0 °C

4.2: 0.83 h / 0 - 95 °C

5.1: caesium carbonate; DavePhos / bis(dibenzylideneacetone)-palladium⁽⁰⁾ / 1,4-dioxane / 24 h / 85 °C

6.1: n-heptane; isopropyl alcohol / Resolution of racemate

With oxalyl dichloride; hydrogen bromide; hydrogen; caesium carbonate; N,N-dimethyl-formamide; DavePhos; sodium nitrite; palladium 10% on activated carbon; bis(dibenzylideneacetone)-palladium⁽⁰⁾; In 1,4-dioxane; ethanol; n-heptane; dichloromethane; water; isopropyl alcohol;

Reference yield:

tert-butyl (2S)-2-[(isopropylamino)carbonyl]-4-[4-(methoxycarbonyl)-2-naphthyl]piperazine-1-carboxylate (954409-67-7) → 3-{(3S)-4-{[1-(3-ethoxyphenyl)-2-(4-methylphenyl)-1H-imidazol-4-yl]carbonyl}-3-[(isopropylamino)carbonyl]-1-piperazinyl}-1-naphthoic acid

Guidance literature:

Multi-step reaction with 3 steps

1: dichloromethane / 1 h

2: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 20 °C

3: lithium hydroxide / tetrahydrofuran; water / 2 h

With lithium hydroxide; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide;

Reference yield:

tert-butyl (2S)-2-[(isopropylamino)carbonyl]-4-[4-(methoxycarbonyl)-2-naphthyl]piperazine-1-carboxylate (954409-67-7) → methyl 3-{(3S)-4-{[1-(3-ethoxyphenyl)-2-(4-methylphenyl)-1H-imidazol-4-yl]carbonyl}-3-[(isopropylamino)carbonyl]-1-piperazinyl}-1-naphthoate trifluoroacetate

Guidance literature:

Multi-step reaction with 2 steps

1: dichloromethane / 1 h

2: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 20 °C

With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; In dichloromethane; N,N-dimethyl-formamide;

upstream raw materials:

3-nitro-1-naphthoic acid

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