(3R,5S,8S)-8-cyclohexyl-18-methoxy-13,13-dimethyl-7,10-dioxo-2,11-dioxa-6,9,21,24-tetraazapentacyclo[15.9.2.13,6.020,27.021,25]nonacosa-1⁽²⁶⁾,17,19,22,24,27-hexaene-5-carboxylic acid

Base Information

• Chemical Name: (3R,5S,8S)-8-cyclohexyl-18-methoxy-13,13-dimethyl-7,10-dioxo-2,11-dioxa-6,9,21,24-tetraazapentacyclo[15.9.2.13,6.020,27.021,25]nonacosa-1⁽²⁶⁾,17,19,22,24,27-hexaene-5-carboxylic acid
• CAS No.: 1103535-61-0
• Molecular Formula: C₃₃H₄₂N₄O₇
• Molecular Weight: 606.719

Synonyms:(3R,5S,8S)-8-cyclohexyl-18-methoxy-13,13-dimethyl-7,10-dioxo-2,11-dioxa-6,9,21,24-tetraazapentacyclo[15.9.2.13,6.020,27.021,25]nonacosa-1⁽²⁶⁾,17,19,22,24,27-hexaene-5-carboxylic acid

Chemical Property of (3R,5S,8S)-8-cyclohexyl-18-methoxy-13,13-dimethyl-7,10-dioxo-2,11-dioxa-6,9,21,24-tetraazapentacyclo[15.9.2.13,6.020,27.021,25]nonacosa-1⁽²⁶⁾,17,19,22,24,27-hexaene-5-carboxylic acid

Chemical Property:

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Technology Process of (3R,5S,8S)-8-cyclohexyl-18-methoxy-13,13-dimethyl-7,10-dioxo-2,11-dioxa-6,9,21,24-tetraazapentacyclo[15.9.2.13,6.020,27.021,25]nonacosa-1⁽²⁶⁾,17,19,22,24,27-hexaene-5-carboxylic acid

There total 5 articles about (3R,5S,8S)-8-cyclohexyl-18-methoxy-13,13-dimethyl-7,10-dioxo-2,11-dioxa-6,9,21,24-tetraazapentacyclo[15.9.2.13,6.020,27.021,25]nonacosa-1⁽²⁶⁾,17,19,22,24,27-hexaene-5-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:

methyl (16S,19S,21R)-16-cyclohexyl-25-methoxy-11,11-dimethyl-14,17-dioxo-9,10,11,12,14,15,16,17,20,21-decahydro-8H,19H-5,7-etheno-18,21-methanoimidazo[1',2':1,6]pyrido[4,3-k][1,10,3,6]dioxadiazacyclononadecine-19-carboxylate (1103535-60-9) → (3R,5S,8S)-8-cyclohexyl-18-methoxy-13,13-dimethyl-7,10-dioxo-2,11-dioxa-6,9,21,24-tetraazapentacyclo[15.9.2.13,6.020,27.021,25]nonacosa-1(26),17,19,22,24,27-hexaene-5-carboxylic acid (1103535-61-0)

Guidance literature:

With hydrogenchloride; LiOH; In tetrahydrofuran; methanol; water;

Reference yield:

methyl (2R,4S,7S)-7-cyclohexyl-23-methoxy-12,12-dimethyl-6,9,20-trioxo-3,4,6,7,8,9,12,13,14,15,19,20-dodecahydro-2H,11H-16,18-etheno-2,5-methanopyrido[4,3-k][1,10,3,6]dioxadiazacyclononadecine-4-carboxylate (1021437-85-3) → (3R,5S,8S)-8-cyclohexyl-18-methoxy-13,13-dimethyl-7,10-dioxo-2,11-dioxa-6,9,21,24-tetraazapentacyclo[15.9.2.13,6.020,27.021,25]nonacosa-1(26),17,19,22,24,27-hexaene-5-carboxylic acid (1103535-61-0)

Guidance literature:

Multi-step reaction with 4 steps

1: pyridine / dichloromethane / 1 h / 0 °C

2: tetrahydrofuran / 36 h / 100 °C

3: acetic acid / 5,5-dimethyl-1,3-cyclohexadiene / 18 h / 140 °C

4: water; lithium hydroxide / methanol / 1 h / 20 °C

With pyridine; water; acetic acid; lithium hydroxide; In tetrahydrofuran; methanol; 5,5-dimethyl-1,3-cyclohexadiene; dichloromethane;

DOI:10.1016/j.bmcl.2012.08.106

Reference yield:

1-tert-butyl 2-methyl (2S,4R)-4-[(7-methoxy-2-oxo-6-vinyl-1,2-dihydroquinolin-4-yl)oxy]pyrrolidine-1,2-dicarboxylate (1021437-77-3) → (3R,5S,8S)-8-cyclohexyl-18-methoxy-13,13-dimethyl-7,10-dioxo-2,11-dioxa-6,9,21,24-tetraazapentacyclo[15.9.2.13,6.020,27.021,25]nonacosa-1(26),17,19,22,24,27-hexaene-5-carboxylic acid (1103535-61-0)

Guidance literature:

Multi-step reaction with 8 steps

1: hydrogenchloride / 1,4-dioxane / 1.5 h / 20 °C

2: N-ethyl-N,N-diisopropylamine; 2-(1H-9-azabenzotriazol-1-yl)-1,1,3,3-tetramethyluroniumhexafluorophosphate / N,N-dimethyl-formamide / 0.25 h

3: Zhan catalyst-1B / dichloromethane / 32 h / 20 °C / Reflux

4: palladium on activated charcoal; hydrogen / ethanol / Inert atmosphere

5: pyridine / dichloromethane / 1 h / 0 °C

6: tetrahydrofuran / 36 h / 100 °C

7: acetic acid / 5,5-dimethyl-1,3-cyclohexadiene / 18 h / 140 °C

8: water; lithium hydroxide / methanol / 1 h / 20 °C

With pyridine; hydrogenchloride; 2-(1H-9-azabenzotriazol-1-yl)-1,1,3,3-tetramethyluroniumhexafluorophosphate; palladium on activated charcoal; water; hydrogen; acetic acid; N-ethyl-N,N-diisopropylamine; lithium hydroxide; In tetrahydrofuran; 1,4-dioxane; methanol; 5,5-dimethyl-1,3-cyclohexadiene; ethanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/j.bmcl.2012.08.106

upstream raw materials:

methyl (16S,19S,21R)-16-cyclohexyl-25-methoxy-11,11-dimethyl-14,17-dioxo-9,10,11,12,14,15,16,17,20,21-decahydro-8H,19H-5,7-etheno-18,21-methanoimidazo[1',2':1,6]pyrido[4,3-k][1,10,3,6]dioxadiazacyclononadecine-19-carboxylate

methyl (2R,4S,7S)-7-cyclohexyl-23-methoxy-12,12-dimethyl-6,9,20-trioxo-3,4,6,7,8,9,12,13,14,15,19,20-dodecahydro-2H,11H-16,18-etheno-2,5-methanopyrido[4,3-k][1,10,3,6]dioxadiazacyclononadecine-4-carboxylate

1-tert-butyl 2-methyl (2S,4R)-4-[(7-methoxy-2-oxo-6-vinyl-1,2-dihydroquinolin-4-yl)oxy]pyrrolidine-1,2-dicarboxylate

methyl (4R)-4-[(7-methoxy-2-oxo-6-vinyl-1,2-dihydroquinolin-4-yl)oxy]-L-prolinate hydrochloride

Downstream raw materials:

C₄₂H₅₄N₆O₉S

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