(S)-9-benzyloxy-2-methyl-3-(p-tosyl)-2,3,4,5-tetrahydro-3-benzazepine-1-one

Base Information

Chemical Name:(S)-9-benzyloxy-2-methyl-3-(p-tosyl)-2,3,4,5-tetrahydro-3-benzazepine-1-one
CAS No.:1253197-67-9
Molecular Formula:C₂₅H₂₅NO₄S
Molecular Weight:435.544
Hs Code.:

Synonyms:(S)-9-benzyloxy-2-methyl-3-(p-tosyl)-2,3,4,5-tetrahydro-3-benzazepine-1-one

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Chemical Property of (S)-9-benzyloxy-2-methyl-3-(p-tosyl)-2,3,4,5-tetrahydro-3-benzazepine-1-one

Chemical Property:

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Technology Process of (S)-9-benzyloxy-2-methyl-3-(p-tosyl)-2,3,4,5-tetrahydro-3-benzazepine-1-one

There total 12 articles about (S)-9-benzyloxy-2-methyl-3-(p-tosyl)-2,3,4,5-tetrahydro-3-benzazepine-1-one 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:

: 1253197-65-7
(S)-2-{N-[2-(3-benzyloxyphenyl)ethyl]-N-(4-tosyl)amino}propionic acid

: 100-39-0
benzyl bromide

: 1253197-67-9
(S)-9-benzyloxy-2-methyl-3-(p-tosyl)-2,3,4,5-tetrahydro-3-benzazepine-1-one

: 1253197-66-8
(S)-7-benzyloxy-2-methyl-3-(p-tosyl)-2,3,4,5-tetrahydro-3-benzazepine-1-one

Guidance literature:: (S)-2-{N-[2-(3-benzyloxyphenyl)ethyl]-N-(4-tosyl)amino}propionic acid; With trifluoroacetic anhydride; In dichloromethane; at -15 ℃; for 0.5h; Inert atmosphere;

With tin(IV) chloride; In dichloromethane; at -15 ℃; Inert atmosphere;

benzyl bromide;

Reference yield:

: 1253197-65-7
(S)-2-{N-[2-(3-benzyloxyphenyl)ethyl]-N-(4-tosyl)amino}propionic acid

: 1253197-67-9
(S)-9-benzyloxy-2-methyl-3-(p-tosyl)-2,3,4,5-tetrahydro-3-benzazepine-1-one

: 1253197-66-8
(S)-7-benzyloxy-2-methyl-3-(p-tosyl)-2,3,4,5-tetrahydro-3-benzazepine-1-one

: 6-benzyloxy-1-methyl-2-(4-tosyl)-1,2,3,4-tetrahydroisoquinoline

Guidance literature:: (S)-2-{N-[2-(3-benzyloxyphenyl)ethyl]-N-(4-tosyl)amino}propionic acid; With trifluoroacetic anhydride; In dichloromethane; at -15 ℃; for 0.5h; Inert atmosphere;

With tin(IV) chloride; In dichloromethane; at -15 ℃; for 24h; Inert atmosphere;

With benzyl bromide; potassium carbonate; In acetone; for 6h; regioselective reaction; Inert atmosphere; Reflux;
DOI:10.1021/acs.jmedchem.5b00897

Reference yield:

: 177259-98-2
2-[(3-(benzyloxy)phenyl)]ethan-1-ol

: 1253197-67-9
(S)-9-benzyloxy-2-methyl-3-(p-tosyl)-2,3,4,5-tetrahydro-3-benzazepine-1-one

: 6-benzyloxy-1-methyl-2-(4-tosyl)-1,2,3,4-tetrahydroisoquinoline

Guidance literature:: Multi-step reaction with 3 steps

1.1: triphenylphosphine; di-isopropyl azodicarboxylate / tetrahydrofuran / 17 h / 0 - 20 °C / Inert atmosphere

2.1: water; lithium hydroxide monohydrate / tetrahydrofuran / 23 h / 20 °C / Inert atmosphere

3.1: trifluoroacetic anhydride / dichloromethane / 0.5 h / -15 °C / Inert atmosphere

3.2: 24 h / -15 °C / Inert atmosphere

3.3: 6 h / Inert atmosphere; Reflux

With lithium hydroxide monohydrate; di-isopropyl azodicarboxylate; water; triphenylphosphine; trifluoroacetic anhydride; In tetrahydrofuran; dichloromethane; 3.1: |Friedel-Crafts Acylation / 3.2: |Friedel-Crafts Acylation;
DOI:10.1021/acs.jmedchem.5b00897