(3S)-2-oxo-3-[[(phenylmethoxy)carbonyl]amino]-1-azetidinesulfonic acid,tetrabutylammonium salt

Base Information

• Chemical Name: (3S)-2-oxo-3-[[(phenylmethoxy)carbonyl]amino]-1-azetidinesulfonic acid,tetrabutylammonium salt
• CAS No.: 80082-47-9
• Molecular Formula: C₁₁H₁₁N₂O₆S*C₁₆H₃₆N
• Molecular Weight: 541.753
• Mol file: 80082-47-9.mol

Synonyms:(3S)-2-oxo-3-[[(phenylmethoxy)carbonyl]amino]-1-azetidinesulfonic acid,tetrabutylammonium salt

Chemical Property of (3S)-2-oxo-3-[[(phenylmethoxy)carbonyl]amino]-1-azetidinesulfonic acid,tetrabutylammonium salt

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3S)-2-oxo-3-[[(phenylmethoxy)carbonyl]amino]-1-azetidinesulfonic acid,tetrabutylammonium salt

There total 12 articles about (3S)-2-oxo-3-[[(phenylmethoxy)carbonyl]amino]-1-azetidinesulfonic acid,tetrabutylammonium salt 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: 92.0%

tetra(n-butyl)ammonium hydrogensulfate (32503-27-8) + benzyl N-[(3S)-2-oxoazetidin-3-yl]carbamate (80082-81-1) → (3S)-2-oxo-3-[[(phenylmethoxy)carbonyl]amino]-1-azetidinesulfonic acid,tetrabutylammonium salt (80082-47-9)

Guidance literature:

With sulfur trioxide-N,N-dimethylformamide complex; In dichloromethane; N,N-dimethyl-formamide; at 0 ℃; for 0.333333h;

DOI:10.1021/jo00147a024

Reference yield: 40.0%

benzyloxycarbonyl-L-β-chloroalanine amide N-sulfonate tetrabutylammonium salt (88144-22-3) → (3S)-2-oxo-3-[[(phenylmethoxy)carbonyl]amino]-1-azetidinesulfonic acid,tetrabutylammonium salt (80082-47-9)

Guidance literature:

With base;

DOI:10.1021/jo00340a048

Reference yield:

benzyl N-[(3S)-2-oxoazetidin-3-yl]carbamate (80082-81-1) → (3S)-2-oxo-3-[[(phenylmethoxy)carbonyl]amino]-1-azetidinesulfonic acid,tetrabutylammonium salt (80082-47-9)

Guidance literature:

With potassium dihydrogenphosphate; sulfur trioxide-N,N-dimethylformamide complex; tetra(n-butyl)ammonium hydrogensulfate; Yield given. Multistep reaction; 1) CH₂Cl₂, DMF, 0 deg C, 20 min, 2) H₂O, pH=4.5;

DOI:10.1016/S0040-4020(01)92151-9

upstream raw materials:

tetra(n-butyl)ammonium hydrogensulfate

(3S)-(benzyloxycarbonyl)amino-2-azetidine-1-sulfonic acid, potassium salt

benzyl N-[(3S)-2-oxoazetidin-3-yl]carbamate

benzyloxycarbonyl-L-β-chloroalanine amide N-sulfonate tetrabutylammonium salt

Refernces

• 1、 Cimarusti,Bonner,Breuer,et al.. "4-alkylated monobactams. Chiral synthesis and antibacterial activity". . p. 2577 - 2589. Retrieved 2007/10/02.
• 2、 Floyd, David M.,Fritz, Alan W.,Pluscec, Josip,Weaver, Eugene R.,Cimarusti, Christopher M.. "Monobactams. Preparation of (S)-3-Amino-2-oxoazetidine-1-sulfonic Acids from L-α-Amino-β-hydroxy Acids via Their Hydroxamic Esters". . p. 5160 - 5167. Retrieved 2007/10/02.