Tazobactam Diphenylmethyl Ester

Base Information

• Chemical Name: Tazobactam Diphenylmethyl Ester
• CAS No.: 89789-07-1
• Molecular Formula: C23H22N4O5S
• Molecular Weight: 466.517
• European Community (EC) Number: 618-304-2
• DSSTox Substance ID: DTXSID001100413
• Mol file: 89789-07-1.mol

Synonyms:Tazobactam Diphenylmethyl Ester;89789-07-1;benzhydryl (2S,3S,5R)-3-methyl-4,4,7-trioxo-3-(triazol-1-ylmethyl)-4lambda6-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate;SCHEMBL1122108;1H-1,2,3-Triazole, 4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid deriv.;DTXSID001100413;EX-A1375;(2S,3S,5R)-Diphenylmethyl 4,4-dioxo-3-(1,2,3-triazol-1-ylmethyl)-2-penicillanate;4-Thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid, 3-methyl-7-oxo-3-(1H-1,2,3-triazol-1-ylmethyl)-, diphenylmethyl ester, 4,4-dioxide, (2S,3S,5R)-;Benzhydryl (2S,3S,5R)-3-((1H-1,2,3-triazol-1-yl)methyl)-3-methyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate 4,4-dioxide

Chemical Property of Tazobactam Diphenylmethyl Ester

Chemical Property:

• Boiling Point: 717.5±70.0 °C(Predicted)
• PKA: 0.85±0.12(Predicted)
• PSA: 119.84000
• Density: 1.47±0.1 g/cm3(Predicted)
• LogP: 2.74370
• XLogP3: 1.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 7
• Exact Mass: 466.13109099
• Heavy Atom Count: 33
• Complexity: 847

Purity/Quality:

99% ^*data from raw suppliers

TAZOBACTAM BENZHYDRYL 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1(C(N2C(S1(=O)=O)CC2=O)C(=O)OC(C3=CC=CC=C3)C4=CC=CC=C4)CN5C=CN=N5
• Isomeric SMILES: C[C@@]1([C@@H](N2[C@H](S1(=O)=O)CC2=O)C(=O)OC(C3=CC=CC=C3)C4=CC=CC=C4)CN5C=CN=N5

Technology Process of Tazobactam Diphenylmethyl Ester

There total 25 articles about Tazobactam Diphenylmethyl 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: 95.7%

2β-(1,2,3-triazol-1-yl) methyl-2α-methyl-6,6-dihydropenicillin-3α-carboxylic acid diphenylmethyl ester → (2S,3S,5R) 3-methyl-7-oxo-3-(1H-1,2,3-triazol-1-yl-methyl)-4-thia-1-azabicyclo[3.2.0]heptane2-carboxylic acid 4,4-dioxide, diphenyl methyl ester (89789-07-1)

Guidance literature:

With sodium tungstate (VI) dihydrate; dihydrogen peroxide; In acetone; at 0.5 - 20 ℃; Concentration; Reagent/catalyst; Temperature;

Reference yield: 93.3%

C23H24N5O5S(1+)*Cl(1-) → (2S,3S,5R) 3-methyl-7-oxo-3-(1H-1,2,3-triazol-1-yl-methyl)-4-thia-1-azabicyclo[3.2.0]heptane2-carboxylic acid 4,4-dioxide, diphenyl methyl ester (89789-07-1)

Guidance literature:

With sodium nitrite; In methanol; water; at 0 ℃; for 3h;

Reference yield: 91.0%

benzhydryl 2β-(azidomethyl)-2α-methylpenam-3α-carboxylate 1,1-dioxide + acetylene (74-86-2,25067-58-7) → (2S,3S,5R) 3-methyl-7-oxo-3-(1H-1,2,3-triazol-1-yl-methyl)-4-thia-1-azabicyclo[3.2.0]heptane2-carboxylic acid 4,4-dioxide, diphenyl methyl ester (89789-07-1)

Guidance literature:

With PVPy-Cu⁺-SO₄^2- (convoluted polymeric pyridine copper(I) catalyst); at 90 ℃; for 24h; Schlenk technique;

DOI:10.1021/acs.oprd.8b00429

upstream raw materials:

trimethylsilylacetylene

(R)-benzhydryl 2-((R)-2-(benzo[d]thiazol-2-yldisulfanyl)-4-oxoazetidin-1-yl)-3-methylbut-3-enoate

benzhydryl 6,6-dihydropenicillate

2β-(chloro)methyl-2α-methyl-6,6-dihydropenam-3α-carboxylic acid benzhydryl ester

Downstream raw materials:

tazobactam acid

tazobactam sodium

Refernces

• 1、 Sun, Tiemin,Wang, Jiasheng,Wu, Chengjun,Xin, Yunting,Zhou, Shuhao. "Application of Continuous Flow in Tazobactam Synthesis". . p. 1648 - 1657. Retrieved 2021/07/19.
• 2、 -. "Tazobactam intermediate, preparation method thereof and method for preparing tazobactam by using intermediate (by machine translation)". . . Retrieved 2020/11/23.