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

Base Information

• Chemical Name: tert-butyl ((1R,3R,4S)-3-acetamido-4-((S)-3-(((benzyloxy)carbonyl)amino)-2-oxopyrrolidin-1-yl)cyclohexyl)carbamate
• CAS No.: 1004536-65-5
• Molecular Formula: C₂₅H₃₆N₄O₆
• Molecular Weight: 488.584

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

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

Chemical Property:

Purity/Quality:

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

There total 7 articles about tert-butyl ((1R,3R,4S)-3-acetamido-4-((S)-3-(((benzyloxy)carbonyl)amino)-2-oxopyrrolidin-1-yl)cyclohexyl)carbamate 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: 84.0%

(1R,2S,5R)-2-((S)-3-(benzyloxycarbonylamino)-2-oxopyrrolidin-1-yl)-5-(tert-butoxycarbonylamino)cyclohexanecarboxamide (1004536-63-3) + acetic anhydride (108-24-7) → tert-butyl ((1R,3R,4S)-3-acetamido-4-((S)-3-(((benzyloxy)carbonyl)amino)-2-oxopyrrolidin-1-yl)cyclohexyl)carbamate (1004536-65-5)

Guidance literature:

With [bis(acetoxy)iodo]benzene; water; N-ethyl-N,N-diisopropylamine; In acetonitrile; at 0 - 10 ℃; for 11.6667h;

Reference yield:

tert-butyl (1R,2S,5R)-2-amino-7-oxo-6-azabicyclo[3.2.1]octane-6-carboxylate (746671-16-9) → tert-butyl ((1R,3R,4S)-3-acetamido-4-((S)-3-(((benzyloxy)carbonyl)amino)-2-oxopyrrolidin-1-yl)cyclohexyl)carbamate (1004536-65-5)

Guidance literature:

Multi-step reaction with 6 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

With lithium hydroxide monohydrate; [bis(acetoxy)iodo]benzene; 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) → tert-butyl ((1R,3R,4S)-3-acetamido-4-((S)-3-(((benzyloxy)carbonyl)amino)-2-oxopyrrolidin-1-yl)cyclohexyl)carbamate (1004536-65-5)

Guidance literature:

Multi-step reaction with 7 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

With lithium hydroxide monohydrate; [bis(acetoxy)iodo]benzene; 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-(benzyloxycarbonylamino)-2-oxopyrrolidin-1-yl)-5-(tert-butoxycarbonylamino)cyclohexanecarboxamide

acetic anhydride

(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

Downstream raw materials:

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

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

benzyl (S)-1-((1S,2R,4R)-2-acetamido-4-(isopropyl-(methyl)amino)cyclohexyl)-2-oxopyrrolidin-3-ylcarbamate

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

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