tert-butyl(2-(N-cyclohexylacrylamido)ethyl)(2-(5-hydroxy-3-oxo-3,4-dihydro-2H-benzo[b][1,4]oxazin-8-yl)ethyl)carbamate

Base Information

• Chemical Name: tert-butyl(2-(N-cyclohexylacrylamido)ethyl)(2-(5-hydroxy-3-oxo-3,4-dihydro-2H-benzo[b][1,4]oxazin-8-yl)ethyl)carbamate
• CAS No.: 1035229-43-6
• Molecular Formula: C₂₆H₃₇N₃O₆
• Molecular Weight: 487.596

Synonyms:tert-butyl(2-(N-cyclohexylacrylamido)ethyl)(2-(5-hydroxy-3-oxo-3,4-dihydro-2H-benzo[b][1,4]oxazin-8-yl)ethyl)carbamate

Chemical Property of tert-butyl(2-(N-cyclohexylacrylamido)ethyl)(2-(5-hydroxy-3-oxo-3,4-dihydro-2H-benzo[b][1,4]oxazin-8-yl)ethyl)carbamate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of tert-butyl(2-(N-cyclohexylacrylamido)ethyl)(2-(5-hydroxy-3-oxo-3,4-dihydro-2H-benzo[b][1,4]oxazin-8-yl)ethyl)carbamate

There total 12 articles about tert-butyl(2-(N-cyclohexylacrylamido)ethyl)(2-(5-hydroxy-3-oxo-3,4-dihydro-2H-benzo[b][1,4]oxazin-8-yl)ethyl)carbamate 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: 17.0%

N-cyclohexyl-N-(2-oxoethyl)acrylamide (1035229-42-5) + 8-(2-aminoethyl)-5-hydroxy-2H-benzo[b][1,4]oxazin-3(4H)-one (1035492-00-2) + di-tert-butyl dicarbonate (24424-99-5) → tert-butyl(2-(N-cyclohexylacrylamido)ethyl)(2-(5-hydroxy-3-oxo-3,4-dihydro-2H-benzo[b][1,4]oxazin-8-yl)ethyl)carbamate (1035229-43-6)

Guidance literature:

N-cyclohexyl-N-(2-oxoethyl)acrylamide; 8-(2-aminoethyl)-5-hydroxy-2H-benzo[b][1,4]oxazin-3(4H)-one; With sodium tris(acetoxy)borohydride; sodium hydrogencarbonate; In 1-methyl-pyrrolidin-2-one; water; at 20 ℃; for 20h; Inert atmosphere;

di-tert-butyl dicarbonate; With sodium hydrogencarbonate; In 1-methyl-pyrrolidin-2-one; water; ethyl acetate; at 20 ℃; for 2h; Inert atmosphere;

DOI:10.1021/acsmedchemlett.5b00124

Reference yield:

N-cyclohexyl-N-(2-oxoethyl)acrylamide (1035229-42-5) + 8‐(2‐aminoethyl)‐5‐hydroxy‐2H‐benzo[b][1,4]oxazin‐3(4H)‐one hydrochloride (1035229-35-6) + di-tert-butyl dicarbonate (24424-99-5) → tert-butyl(2-(N-cyclohexylacrylamido)ethyl)(2-(5-hydroxy-3-oxo-3,4-dihydro-2H-benzo[b][1,4]oxazin-8-yl)ethyl)carbamate (1035229-43-6)

Guidance literature:

N-cyclohexyl-N-(2-oxoethyl)acrylamide; 8‐(2‐aminoethyl)‐5‐hydroxy‐2H‐benzo[b][1,4]oxazin‐3(4H)‐one hydrochloride; With sodium hydrogencarbonate; In 1-methyl-pyrrolidin-2-one; water; for 0.25h;

With sodium tris(acetoxy)borohydride; In 1-methyl-pyrrolidin-2-one; water; for 20h;

di-tert-butyl dicarbonate; With water; sodium hydrogencarbonate; In 1-methyl-pyrrolidin-2-one; for 2h;

Reference yield:

2-nitroresorcinol (601-89-8) → tert-butyl(2-(N-cyclohexylacrylamido)ethyl)(2-(5-hydroxy-3-oxo-3,4-dihydro-2H-benzo[b][1,4]oxazin-8-yl)ethyl)carbamate (1035229-43-6)

Guidance literature:

Multi-step reaction with 8 steps

1.1: aluminum (III) chloride / nitrobenzene / 5 h / 100 °C / Inert atmosphere

2.1: sodium hydrogencarbonate / acetonitrile / 6.5 h / 60 °C / Inert atmosphere; Reflux

3.1: acetic acid; zinc / 2.25 h / 40 °C / Inert atmosphere

4.1: sodium hydrogencarbonate / N,N-dimethyl-formamide / 2 h / Inert atmosphere

4.2: 20 h / 100 °C / Inert atmosphere

5.1: N,N,N-trimethylbenzenemethanaminium dichloroiodate / dichloromethane; acetic acid; water / 20 h / 65 °C / Inert atmosphere

6.1: sodium azide / N,N-dimethyl-formamide / 2 h / 20 °C / Inert atmosphere

7.1: palladium 10% on activated carbon; hydrogenchloride; hydrogen / acetic acid; water / 26 h / 3750.38 Torr

8.1: sodium hydrogencarbonate; sodium tris(acetoxy)borohydride / water; 1-methyl-pyrrolidin-2-one / 20 h / 20 °C / Inert atmosphere

8.2: 2 h / 20 °C / Inert atmosphere

With hydrogenchloride; aluminum (III) chloride; sodium azide; palladium 10% on activated carbon; hydrogen; sodium tris(acetoxy)borohydride; sodium hydrogencarbonate; N,N,N-trimethylbenzenemethanaminium dichloroiodate; acetic acid; zinc; In 1-methyl-pyrrolidin-2-one; dichloromethane; water; acetic acid; nitrobenzene; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1021/acsmedchemlett.5b00124

upstream raw materials:

N-cyclohexyl-N-(2-oxoethyl)acrylamide

8‐(2‐aminoethyl)‐5‐hydroxy‐2H‐benzo[b][1,4]oxazin‐3(4H)‐one hydrochloride

di-tert-butyl dicarbonate

8-(2-aminoethyl)-5-hydroxy-2H-benzo[b][1,4]oxazin-3(4H)-one

Downstream raw materials:

3-(3-chlorophenethoxy)-N-cyclohexyl-N-(2-(2-(5-hydroxy-3-oxo-3,4-dihydro-2H-benzo[b][1,4]oxazin-8-yl)ethylamino)ethyl)propanamide trifluoroacetate

N-cyclohexyl-N-(2-((2-(5-hydroxy-3-oxo-3,4-dihydro-2H-benzo[b][1,4]oxazin-8-yl)ethyl)amino)ethyl)-3-(phenethylamino)-propanamide

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