N-(tetrahydro-2H-pyran-2-yloxy) (E)-4-[3'-(1-adamantyl)-4'-benzyloxyphenyl]-3-chlorocinnamamide

Base Information

Chemical Name:N-(tetrahydro-2H-pyran-2-yloxy) (E)-4-[3'-(1-adamantyl)-4'-benzyloxyphenyl]-3-chlorocinnamamide
CAS No.:943141-71-7
Molecular Formula:C₃₇H₄₀ClNO₄
Molecular Weight:598.182
Hs Code.:

Synonyms:N-(tetrahydro-2H-pyran-2-yloxy) (E)-4-[3'-(1-adamantyl)-4'-benzyloxyphenyl]-3-chlorocinnamamide

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Chemical Property of N-(tetrahydro-2H-pyran-2-yloxy) (E)-4-[3'-(1-adamantyl)-4'-benzyloxyphenyl]-3-chlorocinnamamide

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Technology Process of N-(tetrahydro-2H-pyran-2-yloxy) (E)-4-[3'-(1-adamantyl)-4'-benzyloxyphenyl]-3-chlorocinnamamide

There total 12 articles about N-(tetrahydro-2H-pyran-2-yloxy) (E)-4-[3'-(1-adamantyl)-4'-benzyloxyphenyl]-3-chlorocinnamamide 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: 46.0%

: 943141-70-6
(E)-4-[3'-(1-adamantyl)-4'-benzyloxyphenyl]-3-chlorocinnamic acid

: 6723-30-4
O-2-tetrahydro-2H-pyranhydroxylamine

: 943141-71-7
N-(tetrahydro-2H-pyran-2-yloxy) (E)-4-[3'-(1-adamantyl)-4'-benzyloxyphenyl]-3-chlorocinnamamide

Guidance literature:: With dmap; diisopropyl-carbodiimide; In chloroform; at 0 - 20 ℃;
DOI:10.1021/jm0613323

Reference yield:

: 103909-79-1
ethyl (E)-3-chloro-4-hydroxycinnamate

: 943141-71-7
N-(tetrahydro-2H-pyran-2-yloxy) (E)-4-[3'-(1-adamantyl)-4'-benzyloxyphenyl]-3-chlorocinnamamide

Guidance literature:: Multi-step reaction with 4 steps

1: 93 percent / pyridine / CH₂Cl₂ / 20 °C

2: 91 percent / LiCl; aq. Na₂CO₃ / tetrakis(triphenylphosphine)palladium / 1,2-dimethoxy-ethane / 24 h / Heating

3: 93 percent / LiOH*H₂O / methanol; tetrahydrofuran; H₂O / 6 h

4: 46 percent / 4-(N,N-dimethylamino)pyridine; diisopropylcarbodiimide / CHCl₃ / 0 - 20 °C

With pyridine; dmap; lithium hydroxide; sodium carbonate; lithium chloride; diisopropyl-carbodiimide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; methanol; 1,2-dimethoxyethane; dichloromethane; chloroform; water; 2: Suzuki-Miyaura coupling;
DOI:10.1021/jm0613323

Reference yield:

: 524937-24-4
(E)-ethyl 3-(3-chloro-4-(trifluoromethylsulphonyloxy)phenyl)acrylate

: 943141-71-7
N-(tetrahydro-2H-pyran-2-yloxy) (E)-4-[3'-(1-adamantyl)-4'-benzyloxyphenyl]-3-chlorocinnamamide

Guidance literature:: Multi-step reaction with 3 steps

1: 91 percent / LiCl; aq. Na₂CO₃ / tetrakis(triphenylphosphine)palladium / 1,2-dimethoxy-ethane / 24 h / Heating

2: 93 percent / LiOH*H₂O / methanol; tetrahydrofuran; H₂O / 6 h

3: 46 percent / 4-(N,N-dimethylamino)pyridine; diisopropylcarbodiimide / CHCl₃ / 0 - 20 °C

With dmap; lithium hydroxide; sodium carbonate; lithium chloride; diisopropyl-carbodiimide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; methanol; 1,2-dimethoxyethane; chloroform; water; 1: Suzuki-Miyaura coupling;
DOI:10.1021/jm0613323