(3S,6S)-6-Cyclohexyl-5,8-dioxo-4,7-diaza-bicyclo[14.3.1]icosa-1⁽¹⁹⁾,16⁽²⁰⁾,17-triene-3-carboxylic acid methyl ester

Base Information

• Chemical Name: (3S,6S)-6-Cyclohexyl-5,8-dioxo-4,7-diaza-bicyclo[14.3.1]icosa-1⁽¹⁹⁾,16⁽²⁰⁾,17-triene-3-carboxylic acid methyl ester
• CAS No.: 371111-73-8
• Molecular Formula: C₂₆H₃₈N₂O₄
• Molecular Weight: 442.599

Synonyms:(3S,6S)-6-Cyclohexyl-5,8-dioxo-4,7-diaza-bicyclo[14.3.1]icosa-1⁽¹⁹⁾,16⁽²⁰⁾,17-triene-3-carboxylic acid methyl ester

Chemical Property of (3S,6S)-6-Cyclohexyl-5,8-dioxo-4,7-diaza-bicyclo[14.3.1]icosa-1⁽¹⁹⁾,16⁽²⁰⁾,17-triene-3-carboxylic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3S,6S)-6-Cyclohexyl-5,8-dioxo-4,7-diaza-bicyclo[14.3.1]icosa-1⁽¹⁹⁾,16⁽²⁰⁾,17-triene-3-carboxylic acid methyl ester

There total 6 articles about (3S,6S)-6-Cyclohexyl-5,8-dioxo-4,7-diaza-bicyclo[14.3.1]icosa-1⁽¹⁹⁾,16⁽²⁰⁾,17-triene-3-carboxylic acid methyl ester 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: 100.0%

(E)-(3S,6S)-6-Cyclohexyl-5,8-dioxo-4,7-diaza-bicyclo[14.3.1]icosa-1(19),14,16(20),17-tetraene-3-carboxylic acid methyl ester (371111-70-5) → (3S,6S)-6-Cyclohexyl-5,8-dioxo-4,7-diaza-bicyclo[14.3.1]icosa-1(19),16(20),17-triene-3-carboxylic acid methyl ester (371111-73-8)

Guidance literature:

With hydrogen; palladium on activated charcoal; In ethanol; at 20 ℃;

DOI:10.1016/j.bmcl.2005.07.033

Reference yield:

L-(3-iodo)phenylalanine methyl ester hydrochloride → (3S,6S)-6-Cyclohexyl-5,8-dioxo-4,7-diaza-bicyclo[14.3.1]icosa-1(19),16(20),17-triene-3-carboxylic acid methyl ester (371111-73-8)

Guidance literature:

Multi-step reaction with 5 steps

1: 84 percent / 3-hydroxy-1,2,3-benzotriazin-4(3H)-one; 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride; 4-methylmorpholine / dimethylformamide; CH₂Cl₂ / -20 °C

2: HCl / dioxane / 20 °C

3: 3-hydroxy-1,2,3-benzotriazin-4(3H)-one; 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride; 4-methylmorpholine / dimethylformamide; CH₂Cl₂ / -20 °C

4: 37 percent / Pd(PPh₃)4; Et₃N / acetonitrile; dimethylformamide / 80 °C

5: 100 percent / H₂ / Pd/C / ethanol / 20 °C

With 4-methyl-morpholine; hydrogenchloride; tetrakis(triphenylphosphine) palladium⁽⁰⁾; hydrogen; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; 3-hydroxy-3,4-dihydrobenzotriazine-4-one; palladium on activated charcoal; In 1,4-dioxane; ethanol; dichloromethane; N,N-dimethyl-formamide; acetonitrile; 4: Heck reaction;

DOI:10.1016/j.bmcl.2005.07.033

Reference yield:

(S)-2-((S)-2-tert-Butoxycarbonylamino-2-cyclohexyl-acetylamino)-3-(3-iodo-phenyl)-propionic acid methyl ester (371111-68-1) → (3S,6S)-6-Cyclohexyl-5,8-dioxo-4,7-diaza-bicyclo[14.3.1]icosa-1(19),16(20),17-triene-3-carboxylic acid methyl ester (371111-73-8)

Guidance literature:

Multi-step reaction with 4 steps

1: HCl / dioxane / 20 °C

2: 3-hydroxy-1,2,3-benzotriazin-4(3H)-one; 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride; 4-methylmorpholine / dimethylformamide; CH₂Cl₂ / -20 °C

3: 37 percent / Pd(PPh₃)4; Et₃N / acetonitrile; dimethylformamide / 80 °C

4: 100 percent / H₂ / Pd/C / ethanol / 20 °C

With 4-methyl-morpholine; hydrogenchloride; tetrakis(triphenylphosphine) palladium⁽⁰⁾; hydrogen; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; 3-hydroxy-3,4-dihydrobenzotriazine-4-one; palladium on activated charcoal; In 1,4-dioxane; ethanol; dichloromethane; N,N-dimethyl-formamide; acetonitrile; 3: Heck reaction;

DOI:10.1016/j.bmcl.2005.07.033

upstream raw materials:

(E)-(3S,6S)-6-Cyclohexyl-5,8-dioxo-4,7-diaza-bicyclo[14.3.1]icosa-1⁽¹⁹⁾,14,16⁽²⁰⁾,17-tetraene-3-carboxylic acid methyl ester

(S)-2-((S)-2-tert-Butoxycarbonylamino-2-cyclohexyl-acetylamino)-3-(3-iodo-phenyl)-propionic acid methyl ester

N-(tert-butoxycarbonyl)-L-cyclohexylglycine

Downstream raw materials:

(S)-(2-{3-[((3S,6S)-6-Cyclohexyl-5,8-dioxo-4,7-diaza-bicyclo[14.3.1]icosa-1⁽¹⁹⁾,16⁽²⁰⁾,17-triene-3-carbonyl)-amino]-2-oxo-hexanoylamino}-acetylamino)-phenyl-acetic acid

(S)-(2-{3-[((3S,6S)-6-Cyclohexyl-5,8-dioxo-4,7-diaza-bicyclo[14.3.1]icosa-1⁽¹⁹⁾,16⁽²⁰⁾,17-triene-3-carbonyl)-amino]-2-oxo-hexanoylamino}-acetylamino)-phenyl-acetic acid tert-butyl ester

(S)-(2-{3-[((3S,6S)-6-Cyclohexyl-5,8-dioxo-4,7-diaza-bicyclo[14.3.1]icosa-1⁽¹⁹⁾,16⁽²⁰⁾,17-triene-3-carbonyl)-amino]-2-hydroxy-hexanoylamino}-acetylamino)-phenyl-acetic acid tert-butyl ester

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