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

Base Information

• Chemical Name: tert-butyl (6S,7R)-6-(azidomethyl)-7-(3,4-dichlorophenyl)-1,4-oxazepane-4-carboxylate
• CAS No.: 1372186-95-2
• Molecular Formula: C₁₇H₂₂Cl₂N₄O₃
• Molecular Weight: 401.293
• Mol file: 1372186-95-2.mol

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

Chemical Property of tert-butyl (6S,7R)-6-(azidomethyl)-7-(3,4-dichlorophenyl)-1,4-oxazepane-4-carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of tert-butyl (6S,7R)-6-(azidomethyl)-7-(3,4-dichlorophenyl)-1,4-oxazepane-4-carboxylate

There total 14 articles about tert-butyl (6S,7R)-6-(azidomethyl)-7-(3,4-dichlorophenyl)-1,4-oxazepane-4-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: 100.0%

tert-butyl (6S,7R)-7-(3,4-dichlorophenyl)-6-{[(methylsulfonyl)oxy]methyl}-1,4-oxazepane-4-carboxylate (1372186-92-9) → tert-butyl (6S,7R)-6-(azidomethyl)-7-(3,4-dichlorophenyl)-1,4-oxazepane-4-carboxylate (1372186-95-2)

Guidance literature:

With sodium azide; In N,N-dimethyl-formamide; at 80 ℃; for 3h;

DOI:10.1016/j.bmc.2015.05.017

Reference yield:

tert-butyl (6S,7R)-7-(3,4-dichlorophenyl)-6-(hydroxymethyl)-1,4-oxazepane-4-carboxylate (1372189-39-3) → tert-butyl (6S,7R)-6-(azidomethyl)-7-(3,4-dichlorophenyl)-1,4-oxazepane-4-carboxylate (1372186-95-2)

Guidance literature:

Multi-step reaction with 2 steps

1: triethylamine / tetrahydrofuran / 2 h / Cooling with ice

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

With sodium azide; triethylamine; In tetrahydrofuran; N,N-dimethyl-formamide;

Reference yield:

3,4-dichlorobenzaldehyde (6287-38-3) → tert-butyl (6S,7R)-6-(azidomethyl)-7-(3,4-dichlorophenyl)-1,4-oxazepane-4-carboxylate (1372186-95-2)

Guidance literature:

Multi-step reaction with 11 steps

1.1: 1,4-diaza-bicyclo[2.2.2]octane / acetonitrile / 48 h / 10 - 35 °C

2.1: triethylamine / methanol / 72 h / 10 - 35 °C

3.1: calcium chloride; sodium tetrahydroborate / ethanol; tetrahydrofuran / 2 h / 35 °C / Cooling with ice

3.2: 0.5 h

4.1: 1H-imidazole / tetrahydrofuran / 2 h / 35 °C / Cooling with ice

5.1: triethylamine / tetrahydrofuran / 1.5 h / 0 °C

6.1: sodium t-butanolate / tetrahydrofuran / 2 h / 35 °C / Cooling with ice

7.1: lithium aluminium tetrahydride; aluminum (III) chloride / diethyl ether; tetrahydrofuran / 3 h / -78 - 0 °C / Inert atmosphere

7.2: 2 h / -78 - 35 °C

8.1: carbonochloridic acid 1-chloro-ethyl ester / acetonitrile / 0.25 h / 10 - 35 °C

8.2: 18 h / 80 °C

8.3: 2 h / 35 °C / Cooling with ice

9.1: CHIRALPAK AD / hexane; ethanol / Resolution of racemate

10.1: triethylamine / tetrahydrofuran / 2 h / Cooling with ice

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

With 1,4-diaza-bicyclo[2.2.2]octane; 1H-imidazole; aluminum (III) chloride; sodium tetrahydroborate; lithium aluminium tetrahydride; sodium azide; carbonochloridic acid 1-chloro-ethyl ester; triethylamine; calcium chloride; sodium t-butanolate; In tetrahydrofuran; methanol; diethyl ether; ethanol; hexane; N,N-dimethyl-formamide; acetonitrile;

upstream raw materials:

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

tert-butyl (6S,7R)-7-(3,4-dichlorophenyl)-6-{[(methylsulfonyl)oxy]methyl}-1,4-oxazepane-4-carboxylate

3,4-dichlorobenzaldehyde

di-tert-butyl dicarbonate

Downstream raw materials:

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

tert-butyl (6R,7R)-6-[(acetylamino)methyl]-7-(3,4-dichlorophenyl)-1,4-oxazepane-4-carboxylate

N-(((6S,7R)-7-(3,4-dichlorophenyl)-1,4-oxazepan-6-yl)methyl)-2-methoxyacetamide hydrochloride

(6R,7R)-tert-butyl 7-(3,4-dichlorophenyl)-6-((2-methoxyacetamido)methyl)-1,4-oxazepane-4-carboxylate