1-Butanaminium, N,N,N-tributyl-, (1R,2S,5R)-2-(aminocarbonyl)-7-oxo-1,6-diazabicyclo[3.2.1]oct-6-yl sulfate

Base Information

• Chemical Name: 1-Butanaminium, N,N,N-tributyl-, (1R,2S,5R)-2-(aminocarbonyl)-7-oxo-1,6-diazabicyclo[3.2.1]oct-6-yl sulfate
• CAS No.: 1192651-80-1
• Molecular Formula: C16H36N.C7H10N3O6S
• Molecular Weight: 506.707
• Mol file: 1192651-80-1.mol

Synonyms:1-Butanaminium, N,N,N-tributyl-, (1R,2S,5R)-2-(aminocarbonyl)-7-oxo-1,6-diazabicyclo[3.2.1]oct-6-yl sulfate;N,N,N-tributyl-1-Butanaminium (1R,2S,5R)-2-(aminocarbonyl)-7-oxo-1,6-diazabicyclo[3.2.1]oct-6-yl sulfate

Chemical Property of 1-Butanaminium, N,N,N-tributyl-, (1R,2S,5R)-2-(aminocarbonyl)-7-oxo-1,6-diazabicyclo[3.2.1]oct-6-yl sulfate

Chemical Property:

• PSA: 141.45000
• Density: 1.12 at 20℃
• LogP: 4.79260

Purity/Quality:

99.9% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1-Butanaminium, N,N,N-tributyl-, (1R,2S,5R)-2-(aminocarbonyl)-7-oxo-1,6-diazabicyclo[3.2.1]oct-6-yl sulfate

There total 58 articles about 1-Butanaminium, N,N,N-tributyl-, (1R,2S,5R)-2-(aminocarbonyl)-7-oxo-1,6-diazabicyclo[3.2.1]oct-6-yl sulfate 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: 95.0%

(1R,2S,5R)-6-(benzyloxy)-7-oxo-1,6-diazabicyclo[3.2.1]octane-2-carboxamide (1192651-49-2) + tetra(n-butyl)ammonium hydrogensulfate (32503-27-8) → ({[(2S,5R)-2-carbamoyl-7-oxo-6-(sulfooxy)-1,6-diazabicyclo[3,2,1]-oct-6-yl]oxy}sulfonyl)tetrabutylammonium salt (1192651-80-1,1416134-53-6)

Guidance literature:

(1R,2S,5R)-6-(benzyloxy)-7-oxo-1,6-diazabicyclo[3.2.1]octane-2-carboxamide; With palladium on activated charcoal; hydrogen; sulfur trioxide trimethylamine complex; triethylamine; In water; isopropyl alcohol; at 35 ℃; for 0.0166667h; under 3750.38 Torr; Flow reactor; Large scale;

tetra(n-butyl)ammonium hydrogensulfate; In water; Pressure; Temperature; Reagent/catalyst; Solvent; Large scale;

Reference yield: 93.1%

(2S,5R)-6-(tert-butyldimethylsilyloxy)-7-oxo-1,6-diazacyclo[3.2.1]octane-2-carboxamide + tetrabutyl ammonium fluoride (429-41-4) → ({[(2S,5R)-2-carbamoyl-7-oxo-6-(sulfooxy)-1,6-diazabicyclo[3,2,1]-oct-6-yl]oxy}sulfonyl)tetrabutylammonium salt (1192651-80-1,1416134-53-6)

Guidance literature:

With sulfur trioxide trimethylamine complex; triethylamine; In water; isopropyl alcohol; at 10 - 20 ℃; for 5h;

Reference yield: 92.7%

N,N-bis(p-methoxy)benzyl (2S,5R)-6-benzyloxy-7-oxo-1,6-diazabicyclo[3.2.1]octane-2-carboxamide + tetrabutylammonium acetate (10534-59-5) → ({[(2S,5R)-2-carbamoyl-7-oxo-6-(sulfooxy)-1,6-diazabicyclo[3,2,1]-oct-6-yl]oxy}sulfonyl)tetrabutylammonium salt (1192651-80-1,1416134-53-6)

Guidance literature:

N,N-bis(p-methoxy)benzyl (2S,5R)-6-benzyloxy-7-oxo-1,6-diazabicyclo[3.2.1]octane-2-carboxamide; With palladium 10% on activated carbon; hydrogen; sulfur trioxide trimethylamine complex; triethylamine; In water; isopropyl alcohol; at 20 ℃; for 1h; under 525.053 - 975.098 Torr;

tetrabutylammonium acetate; With acetic acid; In water; at 20 ℃;

upstream raw materials:

(1R,2S,5R)-6-(benzyloxy)-7-oxo-1,6-diazabicyclo[3.2.1]octane-2-carboxamide

tetrabutylammonium acetate

(2S,5R)-5-(benzyloxyamino)-piperidine-2-carboxylic acid amide

(2S,5R)-5-benzyloxyaminopiperidin-2-carboxylic acid benzyl ester oxalic acid salt

Downstream raw materials:

(2S,5R)-1,6-diazabicyclo[3.2.1]octane-2-carboxamide 7-oxo-6-(sulfoxy)monosodium salt

sulfuric acid [(1R,2S,5R)-2-aminocarbonyl-7-oxo-1,6-azabicyclo[3.2.1]oct-6-yl]ester sodium salt

Refernces

• 1、 -. "Preparation method of avibatan intermediate". Paragraph 0102-0105. . Retrieved 2019/05/08.
• 2、 -. "Preparation method of beta-lactamase inhibitor drug avibactam sodium intermediate". Paragraph 0051-0087. . Retrieved 2020/01/03.