1-Azetidinesulfonic acid, 2-oxo-3-[[(phenylmethoxy)carbonyl]amino]-, (S)-, compd. with pyridine (1:1)

Base Information

• Chemical Name: 1-Azetidinesulfonic acid, 2-oxo-3-[[(phenylmethoxy)carbonyl]amino]-, (S)-, compd. with pyridine (1:1)
• CAS No.: 80082-83-3
• Molecular Formula: C11H12N2O6S.C5H5N
• Molecular Weight: 379.393
• Mol file: 80082-83-3.mol

Synonyms:

Chemical Property of 1-Azetidinesulfonic acid, 2-oxo-3-[[(phenylmethoxy)carbonyl]amino]-, (S)-, compd. with pyridine (1:1)

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 1-Azetidinesulfonic acid, 2-oxo-3-[[(phenylmethoxy)carbonyl]amino]-, (S)-, compd. with pyridine (1:1)

There total 6 articles about 1-Azetidinesulfonic acid, 2-oxo-3-[[(phenylmethoxy)carbonyl]amino]-, (S)-, compd. with pyridine (1:1) 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: 100.0%

benzyl N-[(3S)-2-oxoazetidin-3-yl]carbamate (80082-81-1) → (3S)-(benzyloxycarbonyl)amino-2-oxo-azetidine-1-sulfonic acid, pyridinium salt (80082-83-3)

Guidance literature:

With sulfur trioxide pyridine complex; In dichloromethane; N,N-dimethyl-formamide; for 2h; Ambient temperature;

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

Reference yield: 80.9%

benzyl N-[(3S)-2-oxoazetidin-3-yl]carbamate (80082-81-1) → (3S)-(benzyloxycarbonyl)amino-2-oxo-azetidine-1-sulfonic acid, pyridinium salt (80082-83-3)

Guidance literature:

In N,N-dimethyl-formamide; for 48h; Ambient temperature;

DOI:10.1248/cpb.31.1874

Reference yield:

(3S)-(benzyloxycarbonyl)amino-α-isopropyl-2-oxoazetidine-1-acetic acid (64319-92-2) → (3S)-(benzyloxycarbonyl)amino-2-oxo-azetidine-1-sulfonic acid, pyridinium salt (80082-83-3)

Guidance literature:

Multi-step reaction with 3 steps

1: Cu(OAc)2*H₂O / acetonitrile / 2.75 h / 65 °C

2: 25 percent / K₂CO₃, NaBH₄ / methanol; H₂O / 2 h / 0 °C

3: 100 percent / Py-SO₃ / CH₂Cl₂; dimethylformamide / 2 h / Ambient temperature

With sodium tetrahydroborate; copper diacetate; sulfur trioxide pyridine complex; potassium carbonate; In methanol; dichloromethane; water; N,N-dimethyl-formamide; acetonitrile;

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

upstream raw materials:

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

methyl 2-<(3S)-3-benzyloxycarbonylamino-2-oxoazetidin-1-yl>-3-methylbut-2-enoate

(3S)-(benzyloxycarbonyl)amino-α-isopropyl-2-oxoazetidine-1-acetic acid

benzyl chloroformate

Downstream raw materials:

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

Refernces

• 1、 Matsuo,Sugawara,Masuya,Kawano,Noguchi,Ochiai. "Synthesis and antibacterial activity of 3-acylamino-2-azetidinone-1-sulfonic acid derivatives". . p. 1874 - 1884. Retrieved 2007/10/02.