BENZHYDRYL 6,6-DIHYDROPENICILLIC ACID 1-OXIDE[TAZOBACTAM INTERMEDIATE]

Base Information

• Chemical Name: BENZHYDRYL 6,6-DIHYDROPENICILLIC ACID 1-OXIDE[TAZOBACTAM INTERMEDIATE]
• CAS No.: 87579-78-0
• Molecular Formula: C21H21 N O4 S
• Molecular Weight: 383.468
• Mol file: 87579-78-0.mol

Synonyms:4-Thia-1-azabicyclo[3.2.0]heptane-2-carboxylicacid, 3,3-dimethyl-7-oxo-, diphenylmethyl ester, 4-oxide, [2S-(2a,5a)]-;(2S,5R)-3,3-Dimethyl-7-oxo-4-thia-1-azabicyclo[3;

Chemical Property of BENZHYDRYL 6,6-DIHYDROPENICILLIC ACID 1-OXIDE[TAZOBACTAM INTERMEDIATE]

Chemical Property:

• Appearance/Colour: Yellow Solid
• Boiling Point: 598.7±50.0 °C(Predicted)
• PKA: -3.44±0.60(Predicted)
• PSA: 82.89000
• Density: 1.37
• LogP: 3.59070
• Storage Temp.: 2-8°C
• Solubility.: Dichloromethane

Purity/Quality:

99% ^*data from raw suppliers

(2S,5R)-3,3-dimethyl-7-oxo-4-oxide-4-Thia-1-azabicyclo[3.2.0]heptane-2-carboxylicAcidDiphenylmethylEster ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: (2S,5R)-3,3-dimethyl-7-oxo-4-oxide-4-Thia-1-azabicyclo[3.2.0]heptane-2-carboxylic Acid Diphenylmethyl Ester is an intermediate in the synthesis of Tazobactam Sodium Salt-13C2,15N1, which is the labelled analogue of Tazobactam Sodium Salt (T010100), which is a β-Lactamase inhibitor, used with β-lactam antibiotics to enhance their effect.

Technology Process of BENZHYDRYL 6,6-DIHYDROPENICILLIC ACID 1-OXIDE[TAZOBACTAM INTERMEDIATE]

There total 14 articles about BENZHYDRYL 6,6-DIHYDROPENICILLIC ACID 1-OXIDE[TAZOBACTAM INTERMEDIATE] 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: 93.1%

6-bromo benzhydryl s-oxopenicillanate → diphenylmethyl (2S,5R,6R)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate 4-oxide (87579-78-0)

Guidance literature:

With sodium tetrahydroborate; In ethanol; at 0 - 25 ℃; for 1.5h; Reagent/catalyst; Solvent;

Reference yield: 91.2%

6α-bromopenicillan-3α-carboxylic acid diphenylmethyl ester-1β-oxide (80353-26-0) → diphenylmethyl (2S,5R,6R)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate 4-oxide (87579-78-0)

Guidance literature:

With ammonium acetate; zinc; In tetrahydrofuran; water; at 20 ℃; for 1h;

DOI:10.1021/acs.oprd.1c00127

Reference yield: 91.0%

6,6-dibromo-2,2-dimethylpenam-3-carboxylic acid 1-oxide diphenylmethyl ester → diphenylmethyl (2S,5R,6R)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate 4-oxide (87579-78-0)

Guidance literature:

With bismuth(III) sulfate; ammonium chloride; aluminium; In methanol; dichloromethane; water; at 20 - 30 ℃; for 5h; Product distribution / selectivity;

upstream raw materials:

6α-bromopenicillan-3α-carboxylic acid diphenylmethyl ester-1β-oxide

6-bromopenicillanic acid

6-Aminopenicillanic Acid

diphenylmethyl 6α-bromopenicillanate

Downstream raw materials:

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

tazobactam acid

(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

(2S,3R,5R)-3-Chlorocarbonyl-3-methyl-4,4,7-trioxo-4λ⁶-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid benzhydryl ester

Refernces

• 1、 -. "Preparation method of tazobactam intermediate". . . Retrieved 2019/05/08.
• 2、 -. "Preparation method of 6-chloropenicillin sulfoxide diphenylmethyl ester and application thereof". . . Retrieved 2018/07/30.