(S)-ethyl 1-(1-azido-2-{[(benzyloxy)carbonyl]amino}ethyl)cyclopropanecarboxylate

Base Information

Chemical Name:(S)-ethyl 1-(1-azido-2-{[(benzyloxy)carbonyl]amino}ethyl)cyclopropanecarboxylate
CAS No.:328405-10-3
Molecular Formula:C₁₆H₂₀N₄O₄
Molecular Weight:332.359
Hs Code.:

Synonyms:(S)-ethyl 1-(1-azido-2-{[(benzyloxy)carbonyl]amino}ethyl)cyclopropanecarboxylate

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Chemical Property of (S)-ethyl 1-(1-azido-2-{[(benzyloxy)carbonyl]amino}ethyl)cyclopropanecarboxylate

Chemical Property:

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Technology Process of (S)-ethyl 1-(1-azido-2-{[(benzyloxy)carbonyl]amino}ethyl)cyclopropanecarboxylate

There total 6 articles about (S)-ethyl 1-(1-azido-2-{[(benzyloxy)carbonyl]amino}ethyl)cyclopropanecarboxylate 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: 85.0%

: 328405-08-9
ethyl 1-[2-(benzyloxycarbonylamino)-1-hydroxyethyl]-cyclopropanecarboxylate

: 328405-10-3
(S)-ethyl 1-(1-azido-2-{[(benzyloxy)carbonyl]amino}ethyl)cyclopropanecarboxylate

Guidance literature:: ethyl 1-[2-(benzyloxycarbonylamino)-1-hydroxyethyl]-cyclopropanecarboxylate; With methanesulfonyl chloride; triethylamine; In dichloromethane; at 5 ℃; for 1h; Inert atmosphere;

With sodium azide; In N,N-dimethyl-formamide; at 80 ℃; for 1h; Inert atmosphere;
DOI:10.1021/jo2002165

Reference yield:

: 129306-05-4
ethyl 1-(2-bromoacetyl)cyclopropanecarboxylate

: 328405-10-3
(S)-ethyl 1-(1-azido-2-{[(benzyloxy)carbonyl]amino}ethyl)cyclopropanecarboxylate

Guidance literature:: Multi-step reaction with 4 steps

1.1: sodium azide / acetonitrile / 20 h / 20 °C / Inert atmosphere

2.1: hydrogenchloride; palladium 10% on activated carbon; hydrogen / ethanol / 2 h / 20 °C / 1551.49 Torr / Autoclave

2.2: 16.33 h / 30 °C / Cooling with ice; Inert atmosphere

3.1: dichloro(benzene)ruthenium(II) dimer; hydrogen; (2,2,2',2'-tetramethyl[4,4'-bibenzo[d][1,3]dioxole]-5,5'-diyl)bis(diphenylphosphine) / ethanol / 18 h / 70 °C / 15001.5 Torr / Autoclave

4.1: methanesulfonyl chloride; triethylamine / dichloromethane / 1 h / 5 °C / Inert atmosphere

4.2: 1 h / 80 °C / Inert atmosphere

With hydrogenchloride; dichloro(benzene)ruthenium(II) dimer; sodium azide; palladium 10% on activated carbon; hydrogen; methanesulfonyl chloride; triethylamine; (2,2,2',2'-tetramethyl[4,4'-bibenzo[d][1,3]dioxole]-5,5'-diyl)bis(diphenylphosphine); In ethanol; dichloromethane; acetonitrile;
DOI:10.1021/jo2002165

Reference yield:

: 1279116-77-6
ethyl 1-(2-azidoacetyl)cyclopropanecarboxylate

: 328405-10-3
(S)-ethyl 1-(1-azido-2-{[(benzyloxy)carbonyl]amino}ethyl)cyclopropanecarboxylate

Guidance literature:: Multi-step reaction with 3 steps

1.1: hydrogenchloride; palladium 10% on activated carbon; hydrogen / ethanol / 2 h / 20 °C / 1551.49 Torr / Autoclave

1.2: 16.33 h / 30 °C / Cooling with ice; Inert atmosphere

2.1: dichloro(benzene)ruthenium(II) dimer; hydrogen; (2,2,2',2'-tetramethyl[4,4'-bibenzo[d][1,3]dioxole]-5,5'-diyl)bis(diphenylphosphine) / ethanol / 18 h / 70 °C / 15001.5 Torr / Autoclave

3.1: methanesulfonyl chloride; triethylamine / dichloromethane / 1 h / 5 °C / Inert atmosphere

3.2: 1 h / 80 °C / Inert atmosphere

With hydrogenchloride; dichloro(benzene)ruthenium(II) dimer; palladium 10% on activated carbon; hydrogen; methanesulfonyl chloride; triethylamine; (2,2,2',2'-tetramethyl[4,4'-bibenzo[d][1,3]dioxole]-5,5'-diyl)bis(diphenylphosphine); In ethanol; dichloromethane;
DOI:10.1021/jo2002165