TETRABUTYLAMMONIUM (2S,3S)-3-{[(BENZYLOXY)CARBONYL]AMINO}-2-METHYL-4-OXOAZETIDINE-1-SULFONATE

Base Information

• Chemical Name: TETRABUTYLAMMONIUM (2S,3S)-3-{[(BENZYLOXY)CARBONYL]AMINO}-2-METHYL-4-OXOAZETIDINE-1-SULFONATE
• CAS No.: 80082-62-8
• Molecular Weight: 555.78
• Mol file: 80082-62-8.mol

Synonyms:TETRABUTYLAMMONIUM (2S,3S)-3-{[(BENZYLOXY)CARBONYL]AMINO}-2-METHYL-4-OXOAZETIDINE-1-SULFONATE

Chemical Property of TETRABUTYLAMMONIUM (2S,3S)-3-{[(BENZYLOXY)CARBONYL]AMINO}-2-METHYL-4-OXOAZETIDINE-1-SULFONATE

Chemical Property:

• PSA: 127.71000
• LogP: 6.41410

Purity/Quality:

98% ^*data from raw suppliers

(2S,3S)-3-Benzyloxycarbonylamino-2-methyl-4-oxo-1-azetidinesulfonicAcidTetrabutylammoniumSalt ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of TETRABUTYLAMMONIUM (2S,3S)-3-{[(BENZYLOXY)CARBONYL]AMINO}-2-METHYL-4-OXOAZETIDINE-1-SULFONATE

There total 19 articles about TETRABUTYLAMMONIUM (2S,3S)-3-{[(BENZYLOXY)CARBONYL]AMINO}-2-METHYL-4-OXOAZETIDINE-1-SULFONATE 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: 99.0%

C16H36N(1+)*C13H17N2O9S2(1-) (80082-56-0) → (3S-trans)-2-Oxo-3-[[(phenylmethoxy)carbonyl]amino]-4-methyl-1-azetidinesulfonic acid,tetrabutylammonium salt (80082-62-8)

Guidance literature:

With potassium hydrogencarbonate; In water; 1,2-dichloro-ethane; for 0.25h; Heating;

DOI:10.1021/jo00340a048

Reference yield: 94.0%

tetra(n-butyl)ammonium hydroxide (2052-49-5) + N-(benzyloxycarbonyl)succinimide (75315-63-8) + (3S-trans)-3-Amino-4-methyl-2-oxo-1-azetidinesulfonic acid (80082-65-1) → (3S-trans)-2-Oxo-3-[[(phenylmethoxy)carbonyl]amino]-4-methyl-1-azetidinesulfonic acid,tetrabutylammonium salt (80082-62-8)

Guidance literature:

N-(benzyloxycarbonyl)succinimide; (3S-trans)-3-Amino-4-methyl-2-oxo-1-azetidinesulfonic acid; With triethylamine; In ethanol; water; at 25 ℃; for 16h;

tetra(n-butyl)ammonium hydroxide; In water;

Reference yield: 94.0%

N-(Benzyloxycarbonyloxy)succinimide (13139-17-8) + tetra(n-butyl)ammonium hydroxide (2052-49-5) + (2R-cis)-3-amino-2-methyl-4-oxo-1-azetidine-sulfonic acid (80582-09-8) → (3S-trans)-2-Oxo-3-[[(phenylmethoxy)carbonyl]amino]-4-methyl-1-azetidinesulfonic acid,tetrabutylammonium salt (80082-62-8)

Guidance literature:

N-(Benzyloxycarbonyloxy)succinimide; (2R-cis)-3-amino-2-methyl-4-oxo-1-azetidine-sulfonic acid; With triethylamine; In ethanol; water; at 25 ℃; for 16h;

tetra(n-butyl)ammonium hydroxide; In water;

upstream raw materials:

C₁₆H₃₆N⁽¹⁺⁾*C₁₃H₁₇N₂O₉S₂^(1-)

(3S,4R)-3-benzyloxycarbonylamino-4-iodomethyl-2-oxoazetidine-1-sulphonic acid tetrabutylammonium salt

(3S,4R)-3-benzyloxycarbonylamino-4-mesyloxymethyl-2-oxoazetidine-1-sulphonic acid tetrabutylammonium salt

(3R,4R)-3-benzyloxycarbonylamino-4-hydroxymethyl-2-oxoazetidine-1-sulphonic acid tetrabutylammonium salt

Downstream raw materials:

(3S-trans)-3-[[(phenylmethoxy)carbonyl]amino]-4-methyl-2-azetidinone

cis-3-benzyloxycarbonylamino-4-methyl-2-oxoazetidine-1-sulphonic acid sodium salt

(3S-trans)-3-Amino-4-methyl-2-oxo-1-azetidinesulfonic acid

Refernces

• 1、 Ding, Pingyu,Duncton, Matthew A. J.,Fan, Dazhong,Gordon, Eric M.,Grygorash, Ruslan,Li, Xianfeng,Low, Eddy,Ni, Zhi-Jie,Qi, Longwu,Sun, Jiawei,Wang, Brian J.,Yu, Guijun. "Toward Orally Absorbed Prodrugs of the Antibiotic Aztreonam. Design of Novel Prodrugs of Sulfate Containing Drugs. Part 2". supporting information. p. 162 - 165. Retrieved 2020/01/31.
• 2、 -. "Crystalline anhydrous aztreonam". . . Retrieved 2008/06/13.