(1R,2R,4R)-2-[(Tert-butoxycarbonyl)amino]-4-[(dimethylamino)carbonyl]cyclohexylcarbamic acid benzyl ester

Base Information

Chemical Name:(1R,2R,4R)-2-[(Tert-butoxycarbonyl)amino]-4-[(dimethylamino)carbonyl]cyclohexylcarbamic acid benzyl ester
CAS No.:1255529-37-3
Molecular Formula:C₂₂H₃₃N₃O₅
Molecular Weight:419.521
Hs Code.:

Synonyms:(1R,2R,4R)-2-[(Tert-butoxycarbonyl)amino]-4-[(dimethylamino)carbonyl]cyclohexylcarbamic acid benzyl ester

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Chemical Property of (1R,2R,4R)-2-[(Tert-butoxycarbonyl)amino]-4-[(dimethylamino)carbonyl]cyclohexylcarbamic acid benzyl ester

Chemical Property:

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Technology Process of (1R,2R,4R)-2-[(Tert-butoxycarbonyl)amino]-4-[(dimethylamino)carbonyl]cyclohexylcarbamic acid benzyl ester

There total 14 articles about (1R,2R,4R)-2-[(Tert-butoxycarbonyl)amino]-4-[(dimethylamino)carbonyl]cyclohexylcarbamic acid benzyl 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: 71.0%

: (1R,3R,4R)-4-(((benzyloxy)carbonyl)amino)-3-((tert-butoxycarbonyl)amino)cyclohexane-1-carboxylic acid

: 506-59-2
N,N-dimethylammonium chloride

: 1255529-37-3
(1R,2R,4R)-2-[(Tert-butoxycarbonyl)amino]-4-[(dimethylamino)carbonyl]cyclohexylcarbamic acid benzyl ester

Guidance literature:: With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; In N,N-dimethyl-formamide; at 0 - 20 ℃; for 2.5h; Inert atmosphere;
DOI:10.1016/j.tet.2017.01.021

Reference yield:

: 123536-66-3
(1S,4S,5S)-4-iodo-6-oxabicyclo<3.2.1>octan-7-one

: 1255529-37-3
(1R,2R,4R)-2-[(Tert-butoxycarbonyl)amino]-4-[(dimethylamino)carbonyl]cyclohexylcarbamic acid benzyl ester

Guidance literature:: Multi-step reaction with 11 steps

1: sodium hydroxide / water

2: ammonium hydroxide / water; ethanol / 45 °C

3: ammonium hydroxide / ethanol / 20 °C / Cooling with ice

4: triphenylphosphine; diethylazodicarboxylate / tetrahydrofuran / 13 h / 0 - 20 °C / Inert atmosphere

5: potassium carbonate; ethanol / 20 °C

6: triethylamine / dichloromethane / 2.25 h / 0 °C / Inert atmosphere

7: sodium azide; 15-crown-5 / N,N-dimethyl-formamide / 24 h / 75 °C

8: palladium 10% on activated carbon; hydrogen / ethanol / 4 h / 20 °C

9: sodium hydrogencarbonate / ethyl acetate; water / 0 - 20 °C

10: sodium ethanolate; water / ethanol / 3 h / 20 °C / Inert atmosphere

11: triethylamine; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / N,N-dimethyl-formamide / 2.5 h / 0 - 20 °C / Inert atmosphere

With ammonium hydroxide; sodium azide; 15-crown-5; ethanol; palladium 10% on activated carbon; water; hydrogen; sodium ethanolate; sodium hydrogencarbonate; potassium carbonate; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; triphenylphosphine; sodium hydroxide; diethylazodicarboxylate; In tetrahydrofuran; ethanol; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide; 4: |Mitsunobu Displacement;
DOI:10.1016/j.tet.2017.01.021

Reference yield:

: 365997-31-5
(1S,3S,6R)-7-oxabicyclo[4.1.0]heptane-3-carboxylic acid ethyl ester

: 1255529-37-3
(1R,2R,4R)-2-[(Tert-butoxycarbonyl)amino]-4-[(dimethylamino)carbonyl]cyclohexylcarbamic acid benzyl ester

Guidance literature:: Multi-step reaction with 10 steps

1: ammonium hydroxide / water; ethanol / 45 °C

2: ammonium hydroxide / ethanol / 20 °C / Cooling with ice

3: triphenylphosphine; diethylazodicarboxylate / tetrahydrofuran / 13 h / 0 - 20 °C / Inert atmosphere

4: potassium carbonate; ethanol / 20 °C

5: triethylamine / dichloromethane / 2.25 h / 0 °C / Inert atmosphere

6: sodium azide; 15-crown-5 / N,N-dimethyl-formamide / 24 h / 75 °C

7: palladium 10% on activated carbon; hydrogen / ethanol / 4 h / 20 °C

8: sodium hydrogencarbonate / ethyl acetate; water / 0 - 20 °C

9: sodium ethanolate; water / ethanol / 3 h / 20 °C / Inert atmosphere

10: triethylamine; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / N,N-dimethyl-formamide / 2.5 h / 0 - 20 °C / Inert atmosphere

With ammonium hydroxide; sodium azide; 15-crown-5; ethanol; palladium 10% on activated carbon; water; hydrogen; sodium ethanolate; sodium hydrogencarbonate; potassium carbonate; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; ethanol; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide; 3: |Mitsunobu Displacement;
DOI:10.1016/j.tet.2017.01.021