87-53-6

Basic information

• Product Name: (2S-cis)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
• Synonyms: (2S-cis)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid;Penicillanic Acid;(2S,5β)-3,3-Dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2β-carboxylic acid;4-Thia-1-azabicyclo(3.2.0)heptane-2-carboxylic acid, 3,3-dimethyl-7-oxo-, (2S-cis)-;Einecs 201-750-3
• CAS NO: 87-53-6
• Molecular Formula: C₈H₁₁NO₃S
• Molecular Weight: 201.24284
• EINECS: 201-750-3
• Mol File: 87-53-6.mol
• Article Data: 15

Chemical Properties

• Melting Point: 208-209 °C
• Boiling Point: 423.8°C at 760 mmHg
• Flash Point: 210.1°C
• Appearance: /
• Density: 1.46g/cm³
• Vapor Pressure: 2.26E-08mmHg at 25°C
• Refractive Index: 1.624
• PKA: 2.43±0.50(Predicted)
• CAS DataBase Reference: (2S-cis)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid(CAS DataBase Reference)
• NIST Chemistry Reference: (2S-cis)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid(87-53-6)
• EPA Substance Registry System: (2S-cis)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid(87-53-6)

Safety Data

• Hazardous Substances Data: 87-53-6(Hazardous Substances Data)

Usage

Definition

ChEBI: A penam that consists of 3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane bearing a carboxy group at position 2 and having (2S,5R)-configuration.

InChI:InChI=1/C8H11NO3S/c1-8(2)6(7(11)12)9-4(10)3-5(9)13-8/h5-6H,3H2,1-2H3,(H,11,12)/t5-,6+/m1/s1

Upstream product

• 20097-86-3 6-chloropenicillanic acid 
• 79-37-8 oxalyl dichloride 
• 38313-33-6 3-phenyl-2-(2-thienyl)acrylic acid 
• 205320-24-7 6,6-dibromopenicillanic acid 
• 205320-26-9 6α-Bromopenicillanic acid 
• 2153-89-1 6α-chloropenicillanic acid 
• 24158-88-1 6,6-dibromopenicillanic acid 
• 5187-94-0 ampicillin trihydrate 
• 551-16-6 6-Aminopenicillanic Acid 
• 24138-28-1 6-bromopenicillanic acid 
• 551-16-6 6-aminopenicillanic acid 
• 139595-42-9 6,6-dibromopenicillanic acid 
• 24138-28-1 (S)-6-Bromo-3,3-dimethyl-7-oxo-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid 
• 2153-89-1 (S)-6-Chloro-3,3-dimethyl-7-oxo-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid 

Downstream Products

• 68373-14-8 sulbactum 
• 20425-27-8 (2S,5R,6R)-6-(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid 
• 793625-09-9 C₈H₁₁NO₄S 
• 89786-04-9 tazobactam acid 
• 69388-84-7 sodium sulbactam 
• 122692-70-0 (2R,4S)-2-Hydroxycarbamoylmethyl-5,5-dimethyl-thiazolidine-4-carboxylic acid 4-methoxy-benzyl ester 
• 122692-67-5 para-methoxybenzyl penicillinate 
• 69388-89-2 penicillanic acid 4-nitro-benzyl ester 

Relevant articles and documents

Method for preparing sulbactam acid

The invention discloses a preparation method of sulbactam acid, hypophosphorous acid is used as a diazotization reaction reagent and a reduction reagent at the same time, a diazotization and reductionreaction one-pot method is realized, and an obtained intermediate is oxidized by potassium permanganate to obtain the sulbactam acid. The product is the sulbactam acid, the generation amount of wastesalt is greatly reduced compared with that of a traditional process, the production cost and the reaction danger coefficient are obviously reduced, and good economic benefits and social values are achieved.

Synthesis method of tazobactam acid

The invention provides a synthesis method of tazobactam acid, and the method comprises the following steps: performing deamination reaction on 6-APA to obtain a compound A; selectively oxidizing the compound A by a Ce(OTf)4/H2O2 oxidation system to obtain a compound B; reacting the compound B with acetic anhydride to obtain a compound C; reacting the compound C with hydrazine hydrate to obtain a compound D; reacting the compound D with methanesulfonyl chloride to obtain a compound E, reacting the compound E with triazole to obtain a compound F, and performing oxidation reaction on the compoundF to obtain the tazobactam acid. The method has the advantages of simple operation steps, cheap and easily available reaction raw materials, short reaction steps, high purity of obtained intermediateproducts and products, purity of the final product tazobactam acid white solid powder of more than 99.5%, high total molar yield, suitability for industrial production, and wide application prospect.

Sulbactam sodium preparation method

The invention relates to a sulbactam sodium preparation method belongs to the technical field of synthesis of beta-lactamase inhibitors. The sulbactam sodium preparation method comprises the steps that 6-amino penicillanic acid (6-APA) is used as a raw material, reacts in strong acid and a sodium nitrite water solution, then reacts under the effects of copper powder and hypophosphorous acid, and then a target product sulbactam sodium is prepared through oxidation and substitution reaction. The reaction process is simple in operation, the method includes few reaction steps, a by-product is reduced, the final reaction yield is high, the treatment difficulty and cost after wastewater production are reduced, the pressure of environmental protection is reduced for enterprises, the product production cost is reduced, and the sulbactam sodium preparation method is suitable for industrial production.