184696-69-3

Basic information

• Product Name: Desacetyl-7-ACA Lactone
• Synonyms: Desacetyl-7-ACA Lactone;Cefazedone Related Impurity 12;Cefmenoxime Impurity 1;(5aR,6R)-6-amino-5a,6-dihydroazeto[2,1-b]furo[3,4-d][1,3]thiazine-1,7(3H,4H)-dione;Cefazedone Impurity 12
• CAS NO: 184696-69-3
• Molecular Formula: C₈H₈N₂O₃S
• Molecular Weight: 212.23
• Mol File: 184696-69-3.mol

Chemical Properties

• Boiling Point: 628.8±55.0 °C(Predicted)
• Appearance: /
• Density: 1.71±0.1 g/cm3(Predicted)
• PKA: 4.51±0.20(Predicted)
• CAS DataBase Reference: Desacetyl-7-ACA Lactone(CAS DataBase Reference)
• NIST Chemistry Reference: Desacetyl-7-ACA Lactone(184696-69-3)
• EPA Substance Registry System: Desacetyl-7-ACA Lactone(184696-69-3)

Safety Data

• Hazardous Substances Data: 184696-69-3(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
Desacetyl-7-ACA Lactone is used as a key intermediate for the production of cephalosporin antibiotics, which are widely utilized for treating a broad range of bacterial infections. Its presence in the synthesis process is vital for creating effective and potent antibiotics that help combat various bacterial diseases.
Used in Research and Development:
In addition to its application in the pharmaceutical industry, Desacetyl-7-ACA Lactone is also used as a research compound for studying the structure, properties, and mechanisms of action of cephalosporin antibiotics. This helps researchers and scientists in understanding the antibiotic's mode of action and developing new, more effective, and targeted treatments for bacterial infections.

Upstream product

• 67-56-1 methanol 
• 957-68-6 7-Aminocephalosporanic acid 

Relevant articles and documents

Synthesis of HR 916 B: The first technically feasible route to the 1-(pivaloyloxy)ethyl esters of cephalosporins

An efficient synthesis of HR 916 B (4), the orally active 1-(RS)-(pivaloyloxy)ethyl prodrug ester of the cephalosporin cefdaloxime, was developed and applied on a multi-kg scale. AMCA (8) was prepared by exchange of the acetoxy group of fermentation product ACA (7) with the nucleophile methanol under acidic conditions. Its 7-amino group was acylated with mixed anhydride 14 to give 15. Carboxylic acid 15 was esterified with iodohydrin ester 27 or bromohydrin ester 30, respectively, to provide the acylal 16. Simultaneous removal of both the amino- and the oximo-protecting group furnished the prodrug HR 916 3, which was purified and stabilized by precipitation of its tosylate salt 4. The overall yield of 4 (ratio 5/6 = 0.65) was 39% relative to AMCA (8) (four steps), 15% relative to ACA (7) (five steps). VCH Verlagsgesellschaft mbH, 1996.