tert-butyl (3R,4S)-3-({(cyclopropyl)[3-({(1R,2R)-2-[(2,3-dihydro-1H-indol-5-yloxy)carbonyl]cyclopropyl}methoxy)-5-(3-methoxypropyl)benzyl]amino}carbonyl)-4-{4-[2-(2,6-dichloro-4-methylphenoxy)ethoxy]phenyl}piperidine-1-carboxylate

Base Information

• Chemical Name: tert-butyl (3R,4S)-3-({(cyclopropyl)[3-({(1R,2R)-2-[(2,3-dihydro-1H-indol-5-yloxy)carbonyl]cyclopropyl}methoxy)-5-(3-methoxypropyl)benzyl]amino}carbonyl)-4-{4-[2-(2,6-dichloro-4-methylphenoxy)ethoxy]phenyl}piperidine-1-carboxylate
• CAS No.: 1087347-32-7
• Molecular Formula: C₅₄H₆₄Cl₂N₂O₉
• Molecular Weight: 956.016

Synonyms:tert-butyl (3R,4S)-3-({(cyclopropyl)[3-({(1R,2R)-2-[(2,3-dihydro-1H-indol-5-yloxy)carbonyl]cyclopropyl}methoxy)-5-(3-methoxypropyl)benzyl]amino}carbonyl)-4-{4-[2-(2,6-dichloro-4-methylphenoxy)ethoxy]phenyl}piperidine-1-carboxylate

Chemical Property of tert-butyl (3R,4S)-3-({(cyclopropyl)[3-({(1R,2R)-2-[(2,3-dihydro-1H-indol-5-yloxy)carbonyl]cyclopropyl}methoxy)-5-(3-methoxypropyl)benzyl]amino}carbonyl)-4-{4-[2-(2,6-dichloro-4-methylphenoxy)ethoxy]phenyl}piperidine-1-carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

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Technology Process of tert-butyl (3R,4S)-3-({(cyclopropyl)[3-({(1R,2R)-2-[(2,3-dihydro-1H-indol-5-yloxy)carbonyl]cyclopropyl}methoxy)-5-(3-methoxypropyl)benzyl]amino}carbonyl)-4-{4-[2-(2,6-dichloro-4-methylphenoxy)ethoxy]phenyl}piperidine-1-carboxylate

There total 28 articles about tert-butyl (3R,4S)-3-({(cyclopropyl)[3-({(1R,2R)-2-[(2,3-dihydro-1H-indol-5-yloxy)carbonyl]cyclopropyl}methoxy)-5-(3-methoxypropyl)benzyl]amino}carbonyl)-4-{4-[2-(2,6-dichloro-4-methylphenoxy)ethoxy]phenyl}piperidine-1-carboxylate 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:

(1R,2R)-2-{[3-{[[((3R,4S)-1-(tert-butoxycarbonyl)-4-{4-[2-(2.6-dichloro-4-methylphenoxy)ethoxy]phenyl}piperidin-3-yl)carbonyl](cyclopropyl)amino]methyl}-5-(3-methoxypropyl)phenoxy]methyl}cyclopropane-1-carboxylic acid (1087347-30-5) + indan-5-ol sodium salt → tert-butyl (3R,4S)-3-({(cyclopropyl)[3-({(1R,2R)-2-[(2,3-dihydro-1H-indol-5-yloxy)carbonyl]cyclopropyl}methoxy)-5-(3-methoxypropyl)benzyl]amino}carbonyl)-4-{4-[2-(2,6-dichloro-4-methylphenoxy)ethoxy]phenyl}piperidine-1-carboxylate (1087347-32-7)

Guidance literature:

(1R,2R)-2-{[3-{[[((3R,4S)-1-(tert-butoxycarbonyl)-4-{4-[2-(2.6-dichloro-4-methylphenoxy)ethoxy]phenyl}piperidin-3-yl)carbonyl](cyclopropyl)amino]methyl}-5-(3-methoxypropyl)phenoxy]methyl}cyclopropane-1-carboxylic acid; With 4-methyl-morpholine; isobutyl chloroformate; In dichloromethane; at -20 ℃; for 0.75h;

indan-5-ol sodium salt; In tetrahydrofuran; dichloromethane; mineral oil; at -15 - 20 ℃; for 18h;

With sodium hydrogencarbonate; In tetrahydrofuran; dichloromethane; water; mineral oil;

Reference yield:

1-(4-bromophenoxy)-2-(2,6-dichloro-4-methylphenoxy)ethane (877995-77-2) → tert-butyl (3R,4S)-3-({(cyclopropyl)[3-({(1R,2R)-2-[(2,3-dihydro-1H-indol-5-yloxy)carbonyl]cyclopropyl}methoxy)-5-(3-methoxypropyl)benzyl]amino}carbonyl)-4-{4-[2-(2,6-dichloro-4-methylphenoxy)ethoxy]phenyl}piperidine-1-carboxylate (1087347-32-7)

Guidance literature:

Multi-step reaction with 11 steps

1.1: n-butyllithium / tetrahydrofuran / 0.5 h / -78 - -70 °C

1.2: 1 h / -70 - 20 °C

1.3: 0.25 h

2.1: sodium carbonate / (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / propan-1-ol; water / 5 h / 80 °C

3.1: magnesium / methanol / 4.5 h / 20 °C / Heating / reflux

5.1: sodium hydroxide / ethanol; water / 18 h / Heating / reflux

5.2: 20 °C / pH < 1

6.1: N-ethyl-N,N-diisopropylamine; HATU / dichloromethane / 18 h / 20 °C

7.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 1 h / 20 °C

8.1: tributylphosphine; 1,1'-azodicarbonyl-dipiperidine / toluene / 18 h / 80 °C

9.1: sodium hydroxide; water / ethanol / 0.08 h / 100 °C / Microwave irradiation

10.1: hydrogenchloride / water; ethyl acetate

11.1: 4-methyl-morpholine; isobutyl chloroformate / dichloromethane / 0.75 h / -20 °C

11.2: 18 h / -15 - 20 °C

With 4-methyl-morpholine; hydrogenchloride; sodium hydroxide; n-butyllithium; tributylphosphine; tetrabutyl ammonium fluoride; water; sodium carbonate; magnesium; N-ethyl-N,N-diisopropylamine; HATU; 1,1'-azodicarbonyl-dipiperidine; isobutyl chloroformate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; In tetrahydrofuran; methanol; propan-1-ol; ethanol; dichloromethane; water; ethyl acetate; toluene;

Reference yield:

3-((tert-butyl(dimethyl)silyl)oxy)-5-[(1E)-3-methoxy-prop-1-en-1-yl]-benzaldehyde (1026786-87-7) → tert-butyl (3R,4S)-3-({(cyclopropyl)[3-({(1R,2R)-2-[(2,3-dihydro-1H-indol-5-yloxy)carbonyl]cyclopropyl}methoxy)-5-(3-methoxypropyl)benzyl]amino}carbonyl)-4-{4-[2-(2,6-dichloro-4-methylphenoxy)ethoxy]phenyl}piperidine-1-carboxylate (1087347-32-7)

Guidance literature:

Multi-step reaction with 9 steps

1.1: magnesium sulfate / dichloromethane / 12 h / 20 °C

2.1: sodium tetrahydroborate / methanol / 3 h / 0 - 20 °C

3.1: hydrogen / palladium 10% on activated carbon / ethyl acetate / 1.5 h

4.1: N-ethyl-N,N-diisopropylamine; HATU / dichloromethane / 18 h / 20 °C

5.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 1 h / 20 °C

6.1: tributylphosphine; 1,1'-azodicarbonyl-dipiperidine / toluene / 18 h / 80 °C

7.1: sodium hydroxide; water / ethanol / 0.08 h / 100 °C / Microwave irradiation

8.1: hydrogenchloride / water; ethyl acetate

9.1: 4-methyl-morpholine; isobutyl chloroformate / dichloromethane / 0.75 h / -20 °C

9.2: 18 h / -15 - 20 °C

With 4-methyl-morpholine; hydrogenchloride; sodium hydroxide; sodium tetrahydroborate; tributylphosphine; tetrabutyl ammonium fluoride; water; hydrogen; magnesium sulfate; N-ethyl-N,N-diisopropylamine; HATU; 1,1'-azodicarbonyl-dipiperidine; isobutyl chloroformate; palladium 10% on activated carbon; In tetrahydrofuran; methanol; ethanol; dichloromethane; water; ethyl acetate; toluene;

upstream raw materials:

(1R,2R)-2-{[3-{[[((3R,4S)-1-(tert-butoxycarbonyl)-4-{4-[2-(2.6-dichloro-4-methylphenoxy)ethoxy]phenyl}piperidin-3-yl)carbonyl](cyclopropyl)amino]methyl}-5-(3-methoxypropyl)phenoxy]methyl}cyclopropane-1-carboxylic acid

1-(4-bromophenoxy)-2-(2,6-dichloro-4-methylphenoxy)ethane

3-hydroxy-5-[(1E)-3-(methyloxy)-1-propen-1-yl]benzaldehyde

3-((tert-butyl(dimethyl)silyl)oxy)-5-[(1E)-3-methoxy-prop-1-en-1-yl]-benzaldehyde

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