[2-(1-{4-[(5S)-(acetylamino-methyl)-2-oxo-oxazolidin-3-yl]-phenyl}-3-aza-bicyclo[3.1.0]hex-3-yl)-2-oxo-ethyl]-carbamic acid tert-butyl ester

Base Information

• Chemical Name: [2-(1-{4-[(5S)-(acetylamino-methyl)-2-oxo-oxazolidin-3-yl]-phenyl}-3-aza-bicyclo[3.1.0]hex-3-yl)-2-oxo-ethyl]-carbamic acid tert-butyl ester
• CAS No.: 1259556-42-7
• Molecular Formula: C₂₄H₃₂N₄O₆
• Molecular Weight: 472.541
• Mol file: 1259556-42-7.mol

Synonyms:[2-(1-{4-[(5S)-(acetylamino-methyl)-2-oxo-oxazolidin-3-yl]-phenyl}-3-aza-bicyclo[3.1.0]hex-3-yl)-2-oxo-ethyl]-carbamic acid tert-butyl ester

Chemical Property of [2-(1-{4-[(5S)-(acetylamino-methyl)-2-oxo-oxazolidin-3-yl]-phenyl}-3-aza-bicyclo[3.1.0]hex-3-yl)-2-oxo-ethyl]-carbamic acid tert-butyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of [2-(1-{4-[(5S)-(acetylamino-methyl)-2-oxo-oxazolidin-3-yl]-phenyl}-3-aza-bicyclo[3.1.0]hex-3-yl)-2-oxo-ethyl]-carbamic acid tert-butyl ester

There total 12 articles about [2-(1-{4-[(5S)-(acetylamino-methyl)-2-oxo-oxazolidin-3-yl]-phenyl}-3-aza-bicyclo[3.1.0]hex-3-yl)-2-oxo-ethyl]-carbamic acid tert-butyl ester 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: 80.0%

BOC-glycine (4530-20-5) + N-{3-[4-(3-aza-bicyclo[3.1.0]hex-1-yl)-phenyl]-2-oxo-oxazolidin-5-(S)-yl-methyl}-acetamide hydrochloride (1259556-30-3) → [2-(1-{4-[(5S)-(acetylamino-methyl)-2-oxo-oxazolidin-3-yl]-phenyl}-3-aza-bicyclo[3.1.0]hex-3-yl)-2-oxo-ethyl]-carbamic acid tert-butyl ester (1259556-42-7)

Guidance literature:

With 4-methyl-morpholine; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; at 0 - 20 ℃;

Reference yield:

4-Bromophenylacetonitrile (16532-79-9) → [2-(1-{4-[(5S)-(acetylamino-methyl)-2-oxo-oxazolidin-3-yl]-phenyl}-3-aza-bicyclo[3.1.0]hex-3-yl)-2-oxo-ethyl]-carbamic acid tert-butyl ester (1259556-42-7)

Guidance literature:

Multi-step reaction with 13 steps

1.1: sodium hexamethyldisilazane / tetrahydrofuran / 0.17 h / -10 °C

1.2: 4 h / -10 - 20 °C

2.1: dimethylsulfide borane complex; boron trifluoride diethyl etherate / tetrahydrofuran / 4 h / 80 °C

2.2: 0 °C

2.3: pH 8

3.1: thionyl chloride / 1,1-dichloroethane / 2 h / 0 - 20 °C

3.2: 0 °C / pH 8

4.1: triethylamine / dichloromethane / 2 h / 0 °C

5.1: sodium t-butanolate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl / tris-(dibenzylideneacetone)dipalladium⁽⁰⁾ / toluene / 4 h / Reflux

6.1: hydrogen / palladium 10% on activated carbon / methanol

7.1: sodium hydrogencarbonate / toluene; water; acetone / 0 - 20 °C

8.1: n-butyllithium / hexane; tetrahydrofuran / 1 h / -78 °C / Inert atmosphere

8.2: -78 - 20 °C

9.1: triethylamine / dichloromethane / 0 - 20 °C

10.1: sodium azide / N,N-dimethyl-formamide / 110 °C

11.1: 16 h / 20 °C

12.1: hydrogenchloride / diethyl ether / 16 h / 20 °C

13.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol; 4-methyl-morpholine / dichloromethane / 0 - 20 °C

With 4-methyl-morpholine; hydrogenchloride; n-butyllithium; thionyl chloride; sodium azide; dimethylsulfide borane complex; boron trifluoride diethyl etherate; hydrogen; sodium hexamethyldisilazane; sodium hydrogencarbonate; benzotriazol-1-ol; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; sodium t-butanolate; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; palladium 10% on activated carbon; In tetrahydrofuran; methanol; diethyl ether; 1,1-dichloroethane; hexane; dichloromethane; water; N,N-dimethyl-formamide; acetone; toluene;

Reference yield:

1-(4-bromophenyl)-3-azabicyclo[3.1.0]hexane (86215-40-9) → [2-(1-{4-[(5S)-(acetylamino-methyl)-2-oxo-oxazolidin-3-yl]-phenyl}-3-aza-bicyclo[3.1.0]hex-3-yl)-2-oxo-ethyl]-carbamic acid tert-butyl ester (1259556-42-7)

Guidance literature:

Multi-step reaction with 10 steps

1.1: triethylamine / dichloromethane / 2 h / 0 °C

2.1: sodium t-butanolate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl / tris-(dibenzylideneacetone)dipalladium⁽⁰⁾ / toluene / 4 h / Reflux

3.1: hydrogen / palladium 10% on activated carbon / methanol

4.1: sodium hydrogencarbonate / toluene; water; acetone / 0 - 20 °C

5.1: n-butyllithium / hexane; tetrahydrofuran / 1 h / -78 °C / Inert atmosphere

5.2: -78 - 20 °C

6.1: triethylamine / dichloromethane / 0 - 20 °C

7.1: sodium azide / N,N-dimethyl-formamide / 110 °C

8.1: 16 h / 20 °C

9.1: hydrogenchloride / diethyl ether / 16 h / 20 °C

10.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol; 4-methyl-morpholine / dichloromethane / 0 - 20 °C

With 4-methyl-morpholine; hydrogenchloride; n-butyllithium; sodium azide; hydrogen; sodium hydrogencarbonate; benzotriazol-1-ol; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; sodium t-butanolate; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; palladium 10% on activated carbon; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; water; N,N-dimethyl-formamide; acetone; toluene;

upstream raw materials:

BOC-glycine

N-{3-[4-(3-aza-bicyclo[3.1.0]hex-1-yl)-phenyl]-2-oxo-oxazolidin-5-(S)-yl-methyl}-acetamide hydrochloride

4-Bromophenylacetonitrile

1-(4-bromophenyl)-3-azabicyclo[3.1.0]hexane

Downstream raw materials:

2-(1-{4-[(5S)-(acetylamino-methyl)-2-oxo-oxazolidin-3-yl]-phenyl}-3-aza-bicyclo[3.1.0]hex-3-yl)-2-oxo-ethyl-amine trifluoroacetate

N-(3-{4-[3-(2-acetylamino-acetyl)-3-aza-bicyclo[3.1.0]hex-1-yl]-phenyl}-2-oxo-oxazolidin-(5S)-ylmethyl)-acetamide

N-(2-(1-(4-((S)-5-(acetamidomethyl)-2-oxooxazolidin-3-yl)phenyl)-3-azabicyclo[3.1.0]hexan-3-yl)-2-oxoethyl)nicotinamide