1S,3R,4S)-(+)-4-azido-3-[(tert-butoxycarbonyl)aMino]cyclohexanecarboxylic acid ethyl ester

Base Information

• Chemical Name: 1S,3R,4S)-(+)-4-azido-3-[(tert-butoxycarbonyl)aMino]cyclohexanecarboxylic acid ethyl ester
• CAS No.: 365997-34-8
• Molecular Formula: C14H24N4O4
• Molecular Weight: 312.369
• Mol file: 365997-34-8.mol

Synonyms:D-1310;Cyclohexanecarboxylic acid,4-azido-3-[[(1,1-dimethylethoxy)carbonyl]amino]-,ethyl ester,(1S,3R,4S);

Chemical Property of 1S,3R,4S)-(+)-4-azido-3-[(tert-butoxycarbonyl)aMino]cyclohexanecarboxylic acid ethyl ester

Chemical Property:

• PSA: 117.87000
• LogP: 2.57896
• Storage Temp.: Refrigerator
• Solubility.: Dichloromethane; Ethyl Acetate

Purity/Quality:

97% ^*data from raw suppliers

ethyl(1S,3R,4S)-4-azido-3-((tert-butoxycarbonyl)amino)cyclohexane-1-carboxylate 97% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: Ethyl (1S,3R,4S)-4-Azido-3-(tert-butoxycarbonylamino)cyclohexane-1-carboxylate is an intermediate in the synthesis of Edoxaban-d6 (E555522), the isotope labelled analog of Edoxaban (E555520); an anticoagulant drug which acts as a direct factor Xa inhibitor.

Technology Process of 1S,3R,4S)-(+)-4-azido-3-[(tert-butoxycarbonyl)aMino]cyclohexanecarboxylic acid ethyl ester

There total 11 articles about 1S,3R,4S)-(+)-4-azido-3-[(tert-butoxycarbonyl)aMino]cyclohexanecarboxylic acid ethyl 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: 76.0%

(1S,3R,4R)-3-[(tert-butoxycarbonyl)amino]-4-[(methylsulfonyl)oxy]cyclohexanecarboxylic acid ethyl ester (365997-36-0) → ethyl (1S,3R,4S)-4-azido-3-(tert-butoxycarbonylamino)-cyclohexane-1-carboxylate (365997-34-8)

Guidance literature:

With sodium azide; N-benzyl-N,N,N-triethylammonium chloride; In N,N-dimethyl-formamide; at 55 - 60 ℃; for 48h;

Reference yield: 58.0%

(1S,3R,4R)-3-[(tert-butoxycarbonyl)amino]-4-[(methylsulfonyl)oxy]cyclohexanecarboxylic acid ethyl ester (365997-36-0) → ethyl (1S,3R,4R)-4-azido-3-(tert-butoxycarbonylamino)cyclohexane-1-carboxylate + ethyl (1S,3R,4S)-4-azido-3-(tert-butoxycarbonylamino)-cyclohexane-1-carboxylate (365997-34-8)

Guidance literature:

With sodium azide; 15-crown-5; In N,N-dimethyl-formamide; at 75 ℃; for 48h;

DOI:10.1016/j.tet.2017.01.021

Reference yield:

ethyl (1S,3R,4R)-3-(tert-butoxycarbonylamino)-4-hydroxycyclohexane-1-carboxylate (365997-33-7) → ethyl (1S,3R,4S)-4-azido-3-(tert-butoxycarbonylamino)-cyclohexane-1-carboxylate (365997-34-8)

Guidance literature:

ethyl (1S,3R,4R)-3-(tert-butoxycarbonylamino)-4-hydroxycyclohexane-1-carboxylate; With methanesulfonyl chloride; triethylamine; In dichloromethane; at -15 - 20 ℃; for 4.33333h;

With hydrogenchloride; In dichloromethane; water; at 0 ℃;

With sodium azide; In DMF (N,N-dimethyl-formamide); at 67 - 75 ℃; for 16h;

upstream raw materials:

(1S,3R,4R)-3-[(tert-butoxycarbonyl)amino]-4-[(methylsulfonyl)oxy]cyclohexanecarboxylic acid ethyl ester

ethyl (1S,3R,4R)-3-(tert-butoxycarbonylamino)-4-hydroxycyclohexane-1-carboxylate

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

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

Downstream raw materials:

ethyl (1S,3R,4S)-4-amino-3-[(tert-butoxycarbonyl)amino]-cyclohexanecarboxylate

ethyl (1S,3R,4S)-4-{[(benzyloxy)carbonyl]amino}-3-[(tert-butoxycarbonyl)amino]cyclohexanecarboxylate

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

tert-butyl N-[(1R,2S,5S)-2-azido-5-[(dimethylamino)carbonyl]cyclohexyl]carbamate