10-cyclohexyl-8,11-dioxo-2-oxa-9,12-diazabicyclo[13.3.1]nonadeca-1⁽¹⁹⁾,15,17-triene-13-carboxylic acid methyl ester

Base Information

• Chemical Name: 10-cyclohexyl-8,11-dioxo-2-oxa-9,12-diazabicyclo[13.3.1]nonadeca-1⁽¹⁹⁾,15,17-triene-13-carboxylic acid methyl ester
• CAS No.: 371111-64-7
• Molecular Formula: C₂₄H₃₄N₂O₅
• Molecular Weight: 430.544

Synonyms:10-cyclohexyl-8,11-dioxo-2-oxa-9,12-diazabicyclo[13.3.1]nonadeca-1⁽¹⁹⁾,15,17-triene-13-carboxylic acid methyl ester

Chemical Property of 10-cyclohexyl-8,11-dioxo-2-oxa-9,12-diazabicyclo[13.3.1]nonadeca-1⁽¹⁹⁾,15,17-triene-13-carboxylic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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Useful:

Technology Process of 10-cyclohexyl-8,11-dioxo-2-oxa-9,12-diazabicyclo[13.3.1]nonadeca-1⁽¹⁹⁾,15,17-triene-13-carboxylic acid methyl ester

There total 5 articles about 10-cyclohexyl-8,11-dioxo-2-oxa-9,12-diazabicyclo[13.3.1]nonadeca-1⁽¹⁹⁾,15,17-triene-13-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: 74.0%

2-[2-cyclohexyl-2-(5-hydroxypentanoylamino)acetylamino]-3-(3-hydroxyphenyl)propionic acid methyl ester (371111-63-6) → 10-cyclohexyl-8,11-dioxo-2-oxa-9,12-diazabicyclo[13.3.1]nonadeca-1(19),15,17-triene-13-carboxylic acid methyl ester (371111-64-7)

Guidance literature:

With tributylphosphine; 1,1'-azodicarbonyl-dipiperidine; In dichloromethane; at 0 - 20 ℃;

DOI:10.1021/jm050323b

Reference yield:

[S,S]-2-(2-tert-butoxycarbonylamino-2-cyclohexylacetylamino)-3-(3-hydroxyphenyl)propionic acid methyl ester (371111-41-0) → 10-cyclohexyl-8,11-dioxo-2-oxa-9,12-diazabicyclo[13.3.1]nonadeca-1(19),15,17-triene-13-carboxylic acid methyl ester (371111-64-7)

Guidance literature:

Multi-step reaction with 3 steps

1: aq. HCl / dioxane / 4 h / 20 °C

2: 0.430 g / 3,4-dihydro-3-hydroxy-4-oxo-1,2,3-benzotriazine; 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride; 4-methylmorpholine / dimethylformamide; CH₂Cl₂ / cooling

3: 74 percent / tri-n-butylphosphine; 1,1'-(azodicarbonyl)dipiperidine / CH₂Cl₂ / 0 - 20 °C

With 4-methyl-morpholine; hydrogenchloride; tributylphosphine; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; 3-hydroxy-3,4-dihydrobenzotriazine-4-one; 1,1'-azodicarbonyl-dipiperidine; In 1,4-dioxane; dichloromethane; N,N-dimethyl-formamide; 3: Mitsunobu reaction;

DOI:10.1021/jm050323b

Reference yield:

(S,S)-C-cyclohexyl-C-[2-(3-hydroxyphenyl)-1-methoxycarbonylethoxycarbamoyl]methyl ammonium chloride → 10-cyclohexyl-8,11-dioxo-2-oxa-9,12-diazabicyclo[13.3.1]nonadeca-1(19),15,17-triene-13-carboxylic acid methyl ester (371111-64-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 0.430 g / 3,4-dihydro-3-hydroxy-4-oxo-1,2,3-benzotriazine; 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride; 4-methylmorpholine / dimethylformamide; CH₂Cl₂ / cooling

2: 74 percent / tri-n-butylphosphine; 1,1'-(azodicarbonyl)dipiperidine / CH₂Cl₂ / 0 - 20 °C

With 4-methyl-morpholine; tributylphosphine; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; 3-hydroxy-3,4-dihydrobenzotriazine-4-one; 1,1'-azodicarbonyl-dipiperidine; In dichloromethane; N,N-dimethyl-formamide; 2: Mitsunobu reaction;

DOI:10.1021/jm050323b

upstream raw materials:

2-[2-cyclohexyl-2-(5-hydroxypentanoylamino)acetylamino]-3-(3-hydroxyphenyl)propionic acid methyl ester

[S,S]-2-(2-tert-butoxycarbonylamino-2-cyclohexylacetylamino)-3-(3-hydroxyphenyl)propionic acid methyl ester

N-(tert-butoxycarbonyl)-L-cyclohexylglycine

methyl (2S)-2-amino-3-(3-hydroxyphenyl)propanoate hydrochloride

Downstream raw materials:

(S)-(2-{3-[((10S,13S)-10-Cyclohexyl-8,11-dioxo-2-oxa-9,12-diaza-bicyclo[13.3.1]nonadeca-1⁽¹⁸⁾,15⁽¹⁹⁾,16-triene-13-carbonyl)-amino]-2-oxo-hexanoylamino}-acetylamino)-phenyl-acetic acid tert-butyl ester

(S)-(2-{3-[((10S,13S)-10-Cyclohexyl-8,11-dioxo-2-oxa-9,12-diaza-bicyclo[13.3.1]nonadeca-1⁽¹⁸⁾,15⁽¹⁹⁾,16-triene-13-carbonyl)-amino]-2-hydroxy-hexanoylamino}-acetylamino)-phenyl-acetic acid tert-butyl ester

10-cyclohexyl-8,11-dioxo-2-oxa-9,12-diazabicyclo[13.3.1]nonadeca-1⁽¹⁹⁾,15,17-triene-13-carboxylic acid

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