12-cyclohexyl-5,5-dimethyl-11,14-dioxo-2,6-dioxa-10,13-diazatricyclo[14.3.1.1^7,10]henicosa-1⁽¹⁹⁾,16⁽²⁰⁾,17-triene-9-carboxylic acid methyl ester

Base Information

• Chemical Name: 12-cyclohexyl-5,5-dimethyl-11,14-dioxo-2,6-dioxa-10,13-diazatricyclo[14.3.1.1^7,10]henicosa-1⁽¹⁹⁾,16⁽²⁰⁾,17-triene-9-carboxylic acid methyl ester
• CAS No.: 367261-09-4
• Molecular Formula: C₂₇H₃₈N₂O₆
• Molecular Weight: 486.609
• Mol file: 367261-09-4.mol

Synonyms:12-cyclohexyl-5,5-dimethyl-11,14-dioxo-2,6-dioxa-10,13-diazatricyclo[14.3.1.1^7,10]henicosa-1⁽¹⁹⁾,16⁽²⁰⁾,17-triene-9-carboxylic acid methyl ester

Chemical Property of 12-cyclohexyl-5,5-dimethyl-11,14-dioxo-2,6-dioxa-10,13-diazatricyclo[14.3.1.1^7,10]henicosa-1⁽¹⁹⁾,16⁽²⁰⁾,17-triene-9-carboxylic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 12-cyclohexyl-5,5-dimethyl-11,14-dioxo-2,6-dioxa-10,13-diazatricyclo[14.3.1.1^7,10]henicosa-1⁽¹⁹⁾,16⁽²⁰⁾,17-triene-9-carboxylic acid methyl ester

There total 8 articles about 12-cyclohexyl-5,5-dimethyl-11,14-dioxo-2,6-dioxa-10,13-diazatricyclo[14.3.1.1^7,10]henicosa-1⁽¹⁹⁾,16⁽²⁰⁾,17-triene-9-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: 40.0%

(2S,4R)-1-{(S)-2-Cyclohexyl-2-[2-(3-hydroxy-phenyl)-acetylamino]-acetyl}-4-(3-hydroxy-1,1-dimethyl-propoxy)-pyrrolidine-2-carboxylic acid methyl ester (426825-47-0) → 12-cyclohexyl-5,5-dimethyl-11,14-dioxo-2,6-dioxa-10,13-diazatricyclo[14.3.1.17,10]henicosa-1(19),16(20),17-triene-9-carboxylic acid methyl ester (367261-09-4)

Guidance literature:

With triphenylphosphine; 1,1'-azodicarbonyl-dipiperidine; In dichloromethane; for 0.333333h;

DOI:10.1021/jo020075g

Reference yield:

2-methyl-1-buten-4-ol (763-32-6) → 12-cyclohexyl-5,5-dimethyl-11,14-dioxo-2,6-dioxa-10,13-diazatricyclo[14.3.1.17,10]henicosa-1(19),16(20),17-triene-9-carboxylic acid methyl ester (367261-09-4)

Guidance literature:

Multi-step reaction with 7 steps

1: 89 percent / NaH; n-Bu₄NI / tetrahydrofuran / 20 °C

2: 69 percent / BF₃*OEt₂ / CH₂Cl₂ / 48 h / 20 °C

3: 100 percent / H₂ / 10percent Pd/C / ethanol; ethyl acetate / 20 °C

4: 3.5 g / 3-hydroxy-1,2,3-benzotriazin-4(3H)-one; 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride; 4-methylmorpholine / dimethylformamide; CH₂Cl₂ / -20 - 20 °C

5: H₂; HCl / 10percent Pd/C / ethanol; dioxane / 1 h / 0 °C

6: 1.6 g / 3-hydroxy-1,2,3-benzotriazin-4(3H)-one; 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride; 4-methylmorpholine / dimethylformamide; CH₂Cl₂ / -20 - 20 °C

7: 40 percent / 1,1'-(azodicarbonyl)dipiperidine; triphenylphosphine / CH₂Cl₂ / 0.33 h

With 4-methyl-morpholine; hydrogenchloride; boron trifluoride diethyl etherate; hydrogen; tetra-(n-butyl)ammonium iodide; sodium hydride; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; 3-hydroxy-3,4-dihydrobenzotriazine-4-one; triphenylphosphine; 1,1'-azodicarbonyl-dipiperidine; 10percent Pd/C; In tetrahydrofuran; 1,4-dioxane; ethanol; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; 7: Mitsunobu reaction;

DOI:10.1021/jo020075g

Reference yield:

(((3-methylbut-3-en-1-yl)oxy)methyl)benzene (58558-53-5) → 12-cyclohexyl-5,5-dimethyl-11,14-dioxo-2,6-dioxa-10,13-diazatricyclo[14.3.1.17,10]henicosa-1(19),16(20),17-triene-9-carboxylic acid methyl ester (367261-09-4)

Guidance literature:

Multi-step reaction with 6 steps

1: 69 percent / BF₃*OEt₂ / CH₂Cl₂ / 48 h / 20 °C

2: 100 percent / H₂ / 10percent Pd/C / ethanol; ethyl acetate / 20 °C

3: 3.5 g / 3-hydroxy-1,2,3-benzotriazin-4(3H)-one; 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride; 4-methylmorpholine / dimethylformamide; CH₂Cl₂ / -20 - 20 °C

4: H₂; HCl / 10percent Pd/C / ethanol; dioxane / 1 h / 0 °C

5: 1.6 g / 3-hydroxy-1,2,3-benzotriazin-4(3H)-one; 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride; 4-methylmorpholine / dimethylformamide; CH₂Cl₂ / -20 - 20 °C

6: 40 percent / 1,1'-(azodicarbonyl)dipiperidine; triphenylphosphine / CH₂Cl₂ / 0.33 h

With 4-methyl-morpholine; hydrogenchloride; boron trifluoride diethyl etherate; hydrogen; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; 3-hydroxy-3,4-dihydrobenzotriazine-4-one; triphenylphosphine; 1,1'-azodicarbonyl-dipiperidine; 10percent Pd/C; In 1,4-dioxane; ethanol; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; 6: Mitsunobu reaction;

DOI:10.1021/jo020075g

upstream raw materials:

(2S,4R)-1-{(S)-2-Cyclohexyl-2-[2-(3-hydroxy-phenyl)-acetylamino]-acetyl}-4-(3-hydroxy-1,1-dimethyl-propoxy)-pyrrolidine-2-carboxylic acid methyl ester

2-methyl-1-buten-4-ol

m-hydroxyphenylacetic acid

(((3-methylbut-3-en-1-yl)oxy)methyl)benzene

Downstream raw materials:

12-cyclohexyl-5,5-dimethyl-11,14-dioxo-2,6-dioxa-10,13-diazatricyclo[14.3.1.1^7,10]henicosa-1⁽¹⁹⁾,16⁽²⁰⁾,17-triene-9-carboxylic acid

{3-[((7R,9S,12S)-12-Cyclohexyl-5,5-dimethyl-11,14-dioxo-2,6-dioxa-10,13-diaza-tricyclo[14.3.1.1^7,10]henicosa-1⁽²⁰⁾,16,18-triene-9-carbonyl)-amino]-2-oxo-hexanoylamino}-acetic acid

{3-[((7R,9S,12S)-12-Cyclohexyl-5,5-dimethyl-11,14-dioxo-2,6-dioxa-10,13-diaza-tricyclo[14.3.1.1^7,10]henicosa-1⁽²⁰⁾,16,18-triene-9-carbonyl)-amino]-2-oxo-hexanoylamino}-acetic acid benzyl ester

(7R,9S,12S)-12-Cyclohexyl-5,5-dimethyl-11,14-dioxo-2,6-dioxa-10,13-diaza-tricyclo[14.3.1.1^7,10]henicosa-1⁽²⁰⁾,16,18-triene-9-carboxylic acid {1-[({[((S)-dimethylcarbamoyl-phenyl-methyl)-carbamoyl]-methyl}-carbamoyl)-hydroxy-methyl]-butyl}-amide