N-{[(6S,7R)-7-(4-chloro-3-fluorophenyl)-1,4-oxazepan-6-yl]methyl}-2-[(2H³)methyloxy]acetamide hydrochloride

Base Information

• Chemical Name: N-{[(6S,7R)-7-(4-chloro-3-fluorophenyl)-1,4-oxazepan-6-yl]methyl}-2-[(2H³)methyloxy]acetamide hydrochloride
• CAS No.: 1372180-04-5
• Molecular Formula: C₁₅H₂₀ClFN₂O₃*ClH
• Molecular Weight: 370.224

Synonyms:N-{[(6S,7R)-7-(4-chloro-3-fluorophenyl)-1,4-oxazepan-6-yl]methyl}-2-[(2H³)methyloxy]acetamide hydrochloride

Chemical Property of N-{[(6S,7R)-7-(4-chloro-3-fluorophenyl)-1,4-oxazepan-6-yl]methyl}-2-[(2H³)methyloxy]acetamide hydrochloride

Chemical Property:

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Technology Process of N-{[(6S,7R)-7-(4-chloro-3-fluorophenyl)-1,4-oxazepan-6-yl]methyl}-2-[(2H³)methyloxy]acetamide hydrochloride

There total 18 articles about N-{[(6S,7R)-7-(4-chloro-3-fluorophenyl)-1,4-oxazepan-6-yl]methyl}-2-[(2H³)methyloxy]acetamide hydrochloride 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: 83.0%

tert-butyl (6R,7R)-7-(4-chloro-3-fluorophenyl)-6-[({[(2H3)methyloxy]acetyl}amino)methyl]-1,4-oxazepane-4-carboxylate (1372189-12-2) → N-{[(6S,7R)-7-(4-chloro-3-fluorophenyl)-1,4-oxazepan-6-yl]methyl}-2-[(2H3)methyloxy]acetamide hydrochloride (1372180-04-5)

Guidance literature:

With hydrogenchloride; In ethyl acetate; at 20 ℃; for 1h;

DOI:10.1016/j.bmc.2016.05.038

Reference yield:

tert-butyl (6S,7R)-7-(3,4-dichlorophenyl)-6-(hydroxymethyl)-1,4-oxazepane-4-carboxylate (1372189-41-7) → N-{[(6S,7R)-7-(4-chloro-3-fluorophenyl)-1,4-oxazepan-6-yl]methyl}-2-[(2H3)methyloxy]acetamide hydrochloride (1372180-04-5)

Guidance literature:

Multi-step reaction with 5 steps

1: triethylamine / tetrahydrofuran / 3 h / Cooling with ice

2: sodium azide / N,N-dimethyl-formamide / 70 °C

3: triphenylphosphine; water / tetrahydrofuran / 10 - 35 °C

4: triethylamine; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol / tetrahydrofuran

5: hydrogenchloride / ethyl acetate / 1 h / 10 - 35 °C

With hydrogenchloride; sodium azide; water; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; triphenylphosphine; In tetrahydrofuran; ethyl acetate; N,N-dimethyl-formamide; 3: Staudinger Reaction;

Reference yield:

(6S,7R)-tert-butyl 6-(azidomethyl)-7-(4-chloro-3-fluorophenyl)-1,4-oxazepane-4-carboxylate (1372187-08-0) → N-{[(6S,7R)-7-(4-chloro-3-fluorophenyl)-1,4-oxazepan-6-yl]methyl}-2-[(2H3)methyloxy]acetamide hydrochloride (1372180-04-5)

Guidance literature:

Multi-step reaction with 3 steps

1: triphenylphosphine; water / tetrahydrofuran / 10 - 35 °C

2: triethylamine; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol / tetrahydrofuran

3: hydrogenchloride / ethyl acetate / 1 h / 10 - 35 °C

With hydrogenchloride; water; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; triphenylphosphine; In tetrahydrofuran; ethyl acetate; 1: Staudinger Reaction;

upstream raw materials:

3-Chloro-4-fluorobenzaldehyde

tert-butyl (6S,7R)-7-(3,4-dichlorophenyl)-6-(hydroxymethyl)-1,4-oxazepane-4-carboxylate

(6S,7R)-tert-butyl 7-(4-chloro-3-fluorophenyl)-6-((methylsulfonyloxy)methyl)-1,4-oxazepane-4-carboxylate

(6S,7R)-tert-butyl 6-(azidomethyl)-7-(4-chloro-3-fluorophenyl)-1,4-oxazepane-4-carboxylate

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