(E)-(1S,4R,6R,13R,14S,18R)-14-tert-Butoxycarbonylamino-18-(7-methoxy-2-phenyl-quinolin-4-yloxy)-13-methyl-2,15-dioxo-12-oxa-3,16-diaza-tricyclo[14.3.0.0^4,6]nonadec-9-ene-4-carboxylic acid methyl ester

Base Information

• Chemical Name: (E)-(1S,4R,6R,13R,14S,18R)-14-tert-Butoxycarbonylamino-18-(7-methoxy-2-phenyl-quinolin-4-yloxy)-13-methyl-2,15-dioxo-12-oxa-3,16-diaza-tricyclo[14.3.0.0^4,6]nonadec-9-ene-4-carboxylic acid methyl ester
• CAS No.: 300831-66-7
• Molecular Formula: C₄₀H₄₈N₄O₉
• Molecular Weight: 728.843

Synonyms:

Chemical Property of (E)-(1S,4R,6R,13R,14S,18R)-14-tert-Butoxycarbonylamino-18-(7-methoxy-2-phenyl-quinolin-4-yloxy)-13-methyl-2,15-dioxo-12-oxa-3,16-diaza-tricyclo[14.3.0.0^4,6]nonadec-9-ene-4-carboxylic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (E)-(1S,4R,6R,13R,14S,18R)-14-tert-Butoxycarbonylamino-18-(7-methoxy-2-phenyl-quinolin-4-yloxy)-13-methyl-2,15-dioxo-12-oxa-3,16-diaza-tricyclo[14.3.0.0^4,6]nonadec-9-ene-4-carboxylic acid methyl ester

There total 5 articles about (E)-(1S,4R,6R,13R,14S,18R)-14-tert-Butoxycarbonylamino-18-(7-methoxy-2-phenyl-quinolin-4-yloxy)-13-methyl-2,15-dioxo-12-oxa-3,16-diaza-tricyclo[14.3.0.0^4,6]nonadec-9-ene-4-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: 41.0%

(1R,2R)-1-{[(2S,4R)-1-((2S,3R)-3-Allyloxy-2-tert-butoxycarbonylamino-butyryl)-4-(7-methoxy-2-phenyl-quinolin-4-yloxy)-pyrrolidine-2-carbonyl]-amino}-2-but-3-enyl-cyclopropanecarboxylic acid methyl ester (300831-65-6) → (E)-(1S,4R,6R,13R,14S,18R)-14-tert-Butoxycarbonylamino-18-(7-methoxy-2-phenyl-quinolin-4-yloxy)-13-methyl-2,15-dioxo-12-oxa-3,16-diaza-tricyclo[14.3.0.04,6]nonadec-9-ene-4-carboxylic acid methyl ester (300831-66-7)

Guidance literature:

Grubbs catalyst first generation; In dichloromethane; for 2h; Heating;

DOI:10.1016/j.jorganchem.2006.09.027

Reference yield:

(2S,3R)-3-Allyloxy-2-tert-butoxycarbonylamino-butyric acid methyl ester (300831-36-1) → (E)-(1S,4R,6R,13R,14S,18R)-14-tert-Butoxycarbonylamino-18-(7-methoxy-2-phenyl-quinolin-4-yloxy)-13-methyl-2,15-dioxo-12-oxa-3,16-diaza-tricyclo[14.3.0.04,6]nonadec-9-ene-4-carboxylic acid methyl ester (300831-66-7)

Guidance literature:

Multi-step reaction with 3 steps

1: 200 mg / LiOH*H₂O / tetrahydrofuran; methanol; H₂O / 2 h / 20 °C

2: 32 percent / DIPEA; HATU / dimethylformamide / 20 h / 20 °C

3: 41 percent / bis(tricyclohexylphosphine)benzylidene Ru(IV) dichloride / CH₂Cl₂ / 2 h / Heating

With lithium hydroxide; N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; Grubbs catalyst first generation; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide;

DOI:10.1016/j.jorganchem.2006.09.027

Reference yield:

Boc-Thr(All)-OH (300831-37-2) → (E)-(1S,4R,6R,13R,14S,18R)-14-tert-Butoxycarbonylamino-18-(7-methoxy-2-phenyl-quinolin-4-yloxy)-13-methyl-2,15-dioxo-12-oxa-3,16-diaza-tricyclo[14.3.0.04,6]nonadec-9-ene-4-carboxylic acid methyl ester (300831-66-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 32 percent / DIPEA; HATU / dimethylformamide / 20 h / 20 °C

2: 41 percent / bis(tricyclohexylphosphine)benzylidene Ru(IV) dichloride / CH₂Cl₂ / 2 h / Heating

With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; Grubbs catalyst first generation; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/j.jorganchem.2006.09.027

upstream raw materials:

(1R,2R)-1-{[(2S,4R)-1-((2S,3R)-3-Allyloxy-2-tert-butoxycarbonylamino-butyryl)-4-(7-methoxy-2-phenyl-quinolin-4-yloxy)-pyrrolidine-2-carbonyl]-amino}-2-but-3-enyl-cyclopropanecarboxylic acid methyl ester

Boc-Thr(All)-OH

(2S,3R)-3-Allyloxy-2-tert-butoxycarbonylamino-butyric acid methyl ester

Boc-Thr-OH

Downstream raw materials:

(E)-(1S,4R,6R,13R,14S,18R)-14-tert-Butoxycarbonylamino-18-(7-methoxy-2-phenyl-quinolin-4-yloxy)-13-methyl-2,15-dioxo-12-oxa-3,16-diaza-tricyclo[14.3.0.0^4,6]nonadec-9-ene-4-carboxylic acid

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