N-((1R,2S,5R)-2-((S)-3-amino-2-oxopyrrolidin-1-yl)-5-(isopropyl(methyl)amino)cyclohexyl)acetamide

Base Information

• Chemical Name: N-((1R,2S,5R)-2-((S)-3-amino-2-oxopyrrolidin-1-yl)-5-(isopropyl(methyl)amino)cyclohexyl)acetamide
• CAS No.: 1004758-02-4
• Molecular Formula: C₁₆H₃₀N₄O₂
• Molecular Weight: 310.44

Synonyms:N-((1R,2S,5R)-2-((S)-3-amino-2-oxopyrrolidin-1-yl)-5-(isopropyl(methyl)amino)cyclohexyl)acetamide

Chemical Property of N-((1R,2S,5R)-2-((S)-3-amino-2-oxopyrrolidin-1-yl)-5-(isopropyl(methyl)amino)cyclohexyl)acetamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N-((1R,2S,5R)-2-((S)-3-amino-2-oxopyrrolidin-1-yl)-5-(isopropyl(methyl)amino)cyclohexyl)acetamide

There total 10 articles about N-((1R,2S,5R)-2-((S)-3-amino-2-oxopyrrolidin-1-yl)-5-(isopropyl(methyl)amino)cyclohexyl)acetamide 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:

(1R,2S,5R)-tert-butyl 2-(benzyloxycarbonylamino)-7-oxo-6-azabicyclo[3.2.1]octane-6-carboxylate (746670-91-7) → N-((1R,2S,5R)-2-((S)-3-amino-2-oxopyrrolidin-1-yl)-5-(isopropyl(methyl)amino)cyclohexyl)acetamide (1004758-02-4)

Guidance literature:

Multi-step reaction with 11 steps

1.1: palladium 10% on activated carbon; hydrogen / ethyl acetate / 36 h / 760.05 Torr

2.1: N-ethyl-N,N-diisopropylamine; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate / acetonitrile / 4 h / 20 °C

3.1: 48 h / 20 °C

4.1: caesium carbonate / dimethyl sulfoxide / 3 h / 20 °C / Inert atmosphere

5.1: lithium hydroxide monohydrate / tetrahydrofuran; water / 20 °C

6.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol / dichloromethane / 2 h / 20 °C

6.2: 0.33 h

7.1: [bis(acetoxy)iodo]benzene / acetonitrile; water / 11 h / 0 - 10 °C

8.1: trifluoroacetic acid / dichloromethane / 2 h / 20 °C

9.1: sodium acetate; sodium cyanoborohydride / methanol / 6 h / 20 °C

10.1: triethylamine; sodium tris(acetoxy)borohydride / dichloromethane / 0.5 h / 0 - 20 °C

11.1: palladium 10% on activated carbon; hydrogen / methanol / 2 h / 760.05 Torr

With lithium hydroxide monohydrate; [bis(acetoxy)iodo]benzene; palladium 10% on activated carbon; hydrogen; sodium acetate; sodium tris(acetoxy)borohydride; sodium cyanoborohydride; benzotriazol-1-ol; caesium carbonate; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; In tetrahydrofuran; methanol; dichloromethane; water; dimethyl sulfoxide; ethyl acetate; acetonitrile;

DOI:10.1021/acsmedchemlett.8b00439

Reference yield:

tert-butyl (1R,2S,5R)-2-amino-7-oxo-6-azabicyclo[3.2.1]octane-6-carboxylate (746671-16-9) → N-((1R,2S,5R)-2-((S)-3-amino-2-oxopyrrolidin-1-yl)-5-(isopropyl(methyl)amino)cyclohexyl)acetamide (1004758-02-4)

Guidance literature:

Multi-step reaction with 10 steps

1.1: N-ethyl-N,N-diisopropylamine; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate / acetonitrile / 4 h / 20 °C

2.1: 48 h / 20 °C

3.1: caesium carbonate / dimethyl sulfoxide / 3 h / 20 °C / Inert atmosphere

4.1: lithium hydroxide monohydrate / tetrahydrofuran; water / 20 °C

5.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol / dichloromethane / 2 h / 20 °C

5.2: 0.33 h

6.1: [bis(acetoxy)iodo]benzene / acetonitrile; water / 11 h / 0 - 10 °C

7.1: trifluoroacetic acid / dichloromethane / 2 h / 20 °C

8.1: sodium acetate; sodium cyanoborohydride / methanol / 6 h / 20 °C

9.1: triethylamine; sodium tris(acetoxy)borohydride / dichloromethane / 0.5 h / 0 - 20 °C

10.1: palladium 10% on activated carbon; hydrogen / methanol / 2 h / 760.05 Torr

With lithium hydroxide monohydrate; [bis(acetoxy)iodo]benzene; palladium 10% on activated carbon; hydrogen; sodium acetate; sodium tris(acetoxy)borohydride; sodium cyanoborohydride; benzotriazol-1-ol; caesium carbonate; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; In tetrahydrofuran; methanol; dichloromethane; water; dimethyl sulfoxide; acetonitrile;

DOI:10.1021/acsmedchemlett.8b00439

Reference yield:

tert-butyl (1R,2S,5R)-2-((S)-2-(((benzyloxy)carbonyl)amino)-4-(methylthio)butanamido)-7-oxo-6-azabicyclo[3.2.1]octane-6-carboxylate (847955-65-1) → N-((1R,2S,5R)-2-((S)-3-amino-2-oxopyrrolidin-1-yl)-5-(isopropyl(methyl)amino)cyclohexyl)acetamide (1004758-02-4)

Guidance literature:

Multi-step reaction with 9 steps

1.1: 48 h / 20 °C

2.1: caesium carbonate / dimethyl sulfoxide / 3 h / 20 °C / Inert atmosphere

3.1: lithium hydroxide monohydrate / tetrahydrofuran; water / 20 °C

4.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol / dichloromethane / 2 h / 20 °C

4.2: 0.33 h

5.1: [bis(acetoxy)iodo]benzene / acetonitrile; water / 11 h / 0 - 10 °C

6.1: trifluoroacetic acid / dichloromethane / 2 h / 20 °C

7.1: sodium acetate; sodium cyanoborohydride / methanol / 6 h / 20 °C

8.1: triethylamine; sodium tris(acetoxy)borohydride / dichloromethane / 0.5 h / 0 - 20 °C

9.1: palladium 10% on activated carbon; hydrogen / methanol / 2 h / 760.05 Torr

With lithium hydroxide monohydrate; [bis(acetoxy)iodo]benzene; palladium 10% on activated carbon; hydrogen; sodium acetate; sodium tris(acetoxy)borohydride; sodium cyanoborohydride; benzotriazol-1-ol; caesium carbonate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; trifluoroacetic acid; In tetrahydrofuran; methanol; dichloromethane; water; dimethyl sulfoxide; acetonitrile;

DOI:10.1021/acsmedchemlett.8b00439

upstream raw materials:

(1R,2S,5R)-tert-butyl 2-(benzyloxycarbonylamino)-7-oxo-6-azabicyclo[3.2.1]octane-6-carboxylate

tert-butyl (1R,2S,5R)-2-amino-7-oxo-6-azabicyclo[3.2.1]octane-6-carboxylate

tert-butyl (1R,2S,5R)-2-((S)-2-(((benzyloxy)carbonyl)amino)-4-(methylthio)butanamido)-7-oxo-6-azabicyclo[3.2.1]octane-6-carboxylate

tert-butyl (1R,2S,5R)-2-((S)-3-(((benzyloxy)carbonyl)amino)-2-oxopyrrolidin-1-yl)-7-oxo-6-azabicyclo[3.2.1]octane-6-carboxylate

Downstream raw materials:

N-((1R,2S,5R)-5-(isopropyl(methyl)amino)-2-((3S)-3-((1-oxido-6-(trifluoromethyl)-4-quinazolinyl)amino)-2-oxo-1-pyrrolidinyl)cyclohexyl)acetamide

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