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

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
• CAS No.: 371111-65-8
• Molecular Formula: C₂₃H₃₂N₂O₅
• Molecular Weight: 416.517

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

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

Chemical Property:

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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

There total 6 articles about 10-cyclohexyl-8,11-dioxo-2-oxa-9,12-diazabicyclo[13.3.1]nonadeca-1⁽¹⁹⁾,15,17-triene-13-carboxylic acid 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: 88.0%

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) → 10-cyclohexyl-8,11-dioxo-2-oxa-9,12-diazabicyclo[13.3.1]nonadeca-1(19),15,17-triene-13-carboxylic acid (371111-65-8)

Guidance literature:

With lithium hydroxide; In tetrahydrofuran; ethanol; at 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 (371111-65-8)

Guidance literature:

Multi-step reaction with 4 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

4: 88 percent / aq. LiOH / tetrahydrofuran; ethanol / 20 °C

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

DOI:10.1021/jm050323b

Reference yield:

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 (371111-65-8)

Guidance literature:

Multi-step reaction with 2 steps

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

2: 88 percent / aq. LiOH / tetrahydrofuran; ethanol / 20 °C

With lithium hydroxide; tributylphosphine; 1,1'-azodicarbonyl-dipiperidine; In tetrahydrofuran; ethanol; dichloromethane; 1: Mitsunobu reaction;

DOI:10.1021/jm050323b

upstream raw materials:

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

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

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

N-(tert-butoxycarbonyl)-L-cyclohexylglycine

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-hydroxy-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-oxo-hexanoylamino}-acetylamino)-phenyl-acetic acid tert-butyl ester

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