(1R,2S,5R)-2-((S)-3-(benzyloxycarbonylamino)-2-oxopyrrolidin-1-yl)-5-(tert-butoxycarbonylamino)cyclohexanecarboxamide

Base Information

• Chemical Name: (1R,2S,5R)-2-((S)-3-(benzyloxycarbonylamino)-2-oxopyrrolidin-1-yl)-5-(tert-butoxycarbonylamino)cyclohexanecarboxamide
• CAS No.: 1004536-63-3
• Molecular Formula: C₂₄H₃₄N₄O₆
• Molecular Weight: 474.557

Synonyms:(1R,2S,5R)-2-((S)-3-(benzyloxycarbonylamino)-2-oxopyrrolidin-1-yl)-5-(tert-butoxycarbonylamino)cyclohexanecarboxamide

Chemical Property of (1R,2S,5R)-2-((S)-3-(benzyloxycarbonylamino)-2-oxopyrrolidin-1-yl)-5-(tert-butoxycarbonylamino)cyclohexanecarboxamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1R,2S,5R)-2-((S)-3-(benzyloxycarbonylamino)-2-oxopyrrolidin-1-yl)-5-(tert-butoxycarbonylamino)cyclohexanecarboxamide

There total 6 articles about (1R,2S,5R)-2-((S)-3-(benzyloxycarbonylamino)-2-oxopyrrolidin-1-yl)-5-(tert-butoxycarbonylamino)cyclohexanecarboxamide 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%

(1R,2S,5R)-2-((S)-3-(((benzyloxy)carbonyl)amino)-2-oxopyrrolidin-1-yl)-5-((tertbutoxycarbonyl)amino)cyclohexane-1-carboxylic acid (1004536-61-1) → (1R,2S,5R)-2-((S)-3-(benzyloxycarbonylamino)-2-oxopyrrolidin-1-yl)-5-(tert-butoxycarbonylamino)cyclohexanecarboxamide (1004536-63-3)

Guidance literature:

With ammonia; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; at 20 ℃; for 2.33333h; pH=> 7;

Reference yield:

tert-butyl (1R,2S,5R)-2-amino-7-oxo-6-azabicyclo[3.2.1]octane-6-carboxylate (746671-16-9) → (1R,2S,5R)-2-((S)-3-(benzyloxycarbonylamino)-2-oxopyrrolidin-1-yl)-5-(tert-butoxycarbonylamino)cyclohexanecarboxamide (1004536-63-3)

Guidance literature:

Multi-step reaction with 5 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

With lithium hydroxide monohydrate; benzotriazol-1-ol; caesium carbonate; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; dichloromethane; water; dimethyl sulfoxide; acetonitrile;

DOI:10.1021/acsmedchemlett.8b00439

Reference yield:

(1R,2S,5R)-tert-butyl 2-(benzyloxycarbonylamino)-7-oxo-6-azabicyclo[3.2.1]octane-6-carboxylate (746670-91-7) → (1R,2S,5R)-2-((S)-3-(benzyloxycarbonylamino)-2-oxopyrrolidin-1-yl)-5-(tert-butoxycarbonylamino)cyclohexanecarboxamide (1004536-63-3)

Guidance literature:

Multi-step reaction with 6 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

With lithium hydroxide monohydrate; palladium 10% on activated carbon; hydrogen; benzotriazol-1-ol; caesium carbonate; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; dichloromethane; water; dimethyl sulfoxide; ethyl acetate; acetonitrile;

DOI:10.1021/acsmedchemlett.8b00439

upstream raw materials:

(1R,2S,5R)-2-((S)-3-(((benzyloxy)carbonyl)amino)-2-oxopyrrolidin-1-yl)-5-((tertbutoxycarbonyl)amino)cyclohexane-1-carboxylic acid

(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

Downstream raw materials:

tert-butyl (1R,3R,4S)-3-amino-4-((S)-3-benzyloxycarbonylamino-2-oxopyrrolidin-1-yl)cyclohexylcarbamate

tert-butyl ((1R,3R,4S)-3-acetamido-4-((S)-3-(((benzyloxy)carbonyl)amino)-2-oxopyrrolidin-1-yl)cyclohexyl)carbamate

benzyl ((S)-1-((1S,2R,4R)-2-acetamido-4-aminocyclohexyl)-2-oxopyrrolidin-3-yl)carbamate

benzyl (S)-1-((1S,2R,4R)-2-acetamido-4-(isopropylamino)cyclohexyl)-2-oxopyrrolidin-3-ylcarbamate

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