(2S,5R)-3α-Chloromethyl-3-methyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2β-carboxylic acid benzhydryl ester

Base Information

• Chemical Name: (2S,5R)-3α-Chloromethyl-3-methyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2β-carboxylic acid benzhydryl ester
• CAS No.: 85573-73-5
• Molecular Formula: C21H20ClNO3S
• Molecular Weight: 401.914
• Mol file: 85573-73-5.mol

Synonyms:(2S,5R)-3α-Chloromethyl-3-methyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2β-carboxylic acid benzhydryl ester

Chemical Property of (2S,5R)-3α-Chloromethyl-3-methyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2β-carboxylic acid benzhydryl ester

Chemical Property:

• Boiling Point: 565.1±50.0 °C(Predicted)
• PKA: -3.84±0.60(Predicted)
• PSA: 71.91000
• Density: 1.36±0.1 g/cm3(Predicted)
• LogP: 3.92840

Purity/Quality:

98% ^*data from raw suppliers

[2S-(2α,3β,5α)]-3-(Chloromethyl)-3-methyl-7-oxo-4-Thia-1-azabicyclo[3.2.0]heptane-2-carboxylicAcidDiphenylmethylEster ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Uses: [2S-(2α,3β,5α)]-3-(Chloromethyl)-3-methyl-7-oxo-4-Thia-1-azabicyclo[3.2.0]heptane-2-carboxylic Acid Diphenylmethyl Ester is an intermediate used in the synthesis of Tazobactam Sodium Salt-15N3 (T010103), which is a β-Lactamase inhibitor, used with β-lactam antibiotics to enhance their effect.

Technology Process of (2S,5R)-3α-Chloromethyl-3-methyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2β-carboxylic acid benzhydryl ester

There total 12 articles about (2S,5R)-3α-Chloromethyl-3-methyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2β-carboxylic acid benzhydryl 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: 92.0%

(R)-2-[2-(benzothiazol-2-yldisulfanyl)-4-oxo-azetidin-1-yl]-3-methyl-butyl-3-enoic acid benzhydryl ester (85573-72-4,87579-79-1) → di(benzothiazol-2-yl)disulfide (120-78-5) + 2β-chloromethyl-2α-methylpenicillin-3α-carboxylic acid diphenylmethyl ester (85573-73-5,115546-67-3)

Guidance literature:

With hydrogenchloride; sodium nitrite; In dichloromethane; water; at 0 ℃; for 2h;

DOI:10.1246/bcsj.62.3046

Reference yield: 90.0%

(R)-2-[2-(benzothiazol-2-yldisulfanyl)-4-oxo-azetidin-1-yl]-3-methyl-butyl-3-enoic acid benzhydryl ester (85573-72-4,87579-79-1) → 2β-chloromethyl-2α-methylpenicillin-3α-carboxylic acid diphenylmethyl ester (85573-73-5,115546-67-3)

Guidance literature:

With copper dichloride; In dichloromethane; for 4h; Ambient temperature;

DOI:10.1055/s-1986-31587

Reference yield:

(R)-2-[2-(benzothiazol-2-yldisulfanyl)-4-oxo-azetidin-1-yl]-3-methyl-butyl-3-enoic acid benzhydryl ester (85573-72-4,87579-79-1) → 2β-(chloro)methyl-2α-methyl-6,6-dihydropenam-3α-carboxylic acid benzhydryl ester (85573-73-5)

Guidance literature:

With hydrogenchloride; sodium nitrite; In dichloromethane; water; at -6 - -2 ℃; for 2h;

upstream raw materials:

(R)-2-[2-(benzothiazol-2-yldisulfanyl)-4-oxo-azetidin-1-yl]-3-methyl-butyl-3-enoic acid benzhydryl ester

6-aminopenicillanic acid

benzhydryl-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate-4-oxide

Benzhydryl 6α-bromopenicillanate-1-oxide

Downstream raw materials:

(2S,3S,5R)-3-(4-methyl-iinidazol-1-ylmethyl)-3-methyl-4,4,7-trioxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid benzhydryl ester

C₂₆H₂₈N₃O₅S⁽¹⁺⁾*I^(1-)

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

Refernces

• 1、 -. "Preparation method of tazobactam". . . Retrieved 2019/02/19.
• 2、 -. "PENICILLIN CRYSTAL AND PROCESS FOR PRODUCING THE SAME". Page/Page column 5-7. . Retrieved 2008/06/13.