(6S,7R)-tert-butyl 7-(4-chloro-3-fluorophenyl)-6-((3-cyano-2-oxopyridin-1(2H)-yl)methyl)-1,4-oxazepane-4-carboxylate

Base Information

• Chemical Name: (6S,7R)-tert-butyl 7-(4-chloro-3-fluorophenyl)-6-((3-cyano-2-oxopyridin-1(2H)-yl)methyl)-1,4-oxazepane-4-carboxylate
• CAS No.: 1372187-14-8
• Molecular Formula: C₂₃H₂₅ClFN₃O₄
• Molecular Weight: 461.921

Synonyms:(6S,7R)-tert-butyl 7-(4-chloro-3-fluorophenyl)-6-((3-cyano-2-oxopyridin-1(2H)-yl)methyl)-1,4-oxazepane-4-carboxylate

Chemical Property of (6S,7R)-tert-butyl 7-(4-chloro-3-fluorophenyl)-6-((3-cyano-2-oxopyridin-1(2H)-yl)methyl)-1,4-oxazepane-4-carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (6S,7R)-tert-butyl 7-(4-chloro-3-fluorophenyl)-6-((3-cyano-2-oxopyridin-1(2H)-yl)methyl)-1,4-oxazepane-4-carboxylate

There total 7 articles about (6S,7R)-tert-butyl 7-(4-chloro-3-fluorophenyl)-6-((3-cyano-2-oxopyridin-1(2H)-yl)methyl)-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: 83.0%

(6S,7R)-tert-butyl 7-(4-chloro-3-fluorophenyl)-6-((methylsulfonyloxy)methyl)-1,4-oxazepane-4-carboxylate (1372187-07-9) + pyrid-2-one-3-carbonitrile (20577-27-9,5657-63-6) → (6S,7R)-tert-butyl 7-(4-chloro-3-fluorophenyl)-6-((3-cyano-2-oxopyridin-1(2H)-yl)methyl)-1,4-oxazepane-4-carboxylate (1372187-14-8)

Guidance literature:

pyrid-2-one-3-carbonitrile; With sodium hydride; In 1,2-dimethoxyethane; N,N-dimethyl-formamide; mineral oil; at 0 ℃; for 0.333333h;

With lithium bromide; In 1,2-dimethoxyethane; N,N-dimethyl-formamide; mineral oil; at 20 ℃; for 1.5h;

(6S,7R)-tert-butyl 7-(4-chloro-3-fluorophenyl)-6-((methylsulfonyloxy)methyl)-1,4-oxazepane-4-carboxylate; In 1,2-dimethoxyethane; N,N-dimethyl-formamide; mineral oil; at 60 ℃;

DOI:10.1016/j.bmc.2016.06.014

Reference yield:

tert-butyl (6S,7R)-7-(3,4-dichlorophenyl)-6-(hydroxymethyl)-1,4-oxazepane-4-carboxylate (1372189-41-7) → (6S,7R)-tert-butyl 7-(4-chloro-3-fluorophenyl)-6-((3-cyano-2-oxopyridin-1(2H)-yl)methyl)-1,4-oxazepane-4-carboxylate (1372187-14-8)

Guidance literature:

Multi-step reaction with 2 steps

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

2.1: sodium hydride / N,N-dimethyl-formamide; 1,2-dimethoxyethane / 0.33 h / Cooling with ice

2.2: 1.5 h / 10 - 35 °C

2.3: 60 °C

With sodium hydride; triethylamine; In tetrahydrofuran; 1,2-dimethoxyethane; N,N-dimethyl-formamide;

Reference yield:

methyl (2RS,3RS)-2-[(benzylamino)methyl]-3-(3-chloro-4-fluorophenyl)-3-hydroxypropanoate → (6S,7R)-tert-butyl 7-(4-chloro-3-fluorophenyl)-6-((3-cyano-2-oxopyridin-1(2H)-yl)methyl)-1,4-oxazepane-4-carboxylate (1372187-14-8)

Guidance literature:

Multi-step reaction with 8 steps

1.1: calcium chloride; sodium tetrahydroborate / ethanol; tetrahydrofuran / 4 h / 35 °C / Cooling with ice

1.2: 1 h

2.1: dmap; triethylamine / tetrahydrofuran / 18 h / 35 °C / Cooling with ice

3.1: triethylamine / tetrahydrofuran / 18 h / 0 °C

3.2: 2 h / 35 °C / Cooling with ice

4.1: lithium aluminium tetrahydride; aluminum (III) chloride / diethyl ether; tetrahydrofuran / 2 h / 0 °C / Inert atmosphere

4.2: -78 - 35 °C

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

5.2: 1 h / Reflux

5.3: 2 h / 10 - 35 °C

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

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

8.1: sodium hydride / N,N-dimethyl-formamide; 1,2-dimethoxyethane / 0.33 h / Cooling with ice

8.2: 1.5 h / 10 - 35 °C

8.3: 60 °C

With dmap; aluminum (III) chloride; sodium tetrahydroborate; lithium aluminium tetrahydride; carbonochloridic acid 1-chloro-ethyl ester; sodium hydride; triethylamine; calcium chloride; In tetrahydrofuran; 1,2-dimethoxyethane; 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

3-Chloro-4-fluorobenzaldehyde

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

pyrid-2-one-3-carbonitrile

Downstream raw materials:

3-(1-(((6S,7R)-7-(4-chloro-3-fluorophenyl)-1,4-oxazepan-6-yl)methyl)-2-oxo-1,2-dihydropyridin-3-yl)-1,2,4-oxadiazol-5(4H)-one hydrochloride

(6S,7R)-tert-butyl 7-(4-chloro-3-fluorophenyl)-6-((2-oxo-3-(5-oxo-4,5-dihydro-1,2,4-oxadiazol-3-yl)pyridin-1(2H)-yl)methyl)-1,4-oxazepane-4-carboxylate

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