105889-80-3

Basic information

• Product Name: (tert-Butoxycarbonyl)oxycefcapene pivoxil
• Synonyms: (tert-Butoxycarbonyl)oxycefcapene pivoxil;Cefcapene Impurity 2;Cefcapene Impurity 9
• CAS NO: 105889-80-3
• Molecular Formula: C₂₈H₃₇N₅O₁₀S₂
• Molecular Weight: 667.75088
• Mol File: 105889-80-3.mol
• Article Data: 5

Chemical Properties

• Appearance: /
• Density: 1.41g/cm³
• Refractive Index: 1.609
• PKA: 4.93±0.70(Predicted)
• CAS DataBase Reference: (tert-Butoxycarbonyl)oxycefcapene pivoxil(CAS DataBase Reference)
• NIST Chemistry Reference: (tert-Butoxycarbonyl)oxycefcapene pivoxil(105889-80-3)
• EPA Substance Registry System: (tert-Butoxycarbonyl)oxycefcapene pivoxil(105889-80-3)

Safety Data

• Hazardous Substances Data: 105889-80-3(Hazardous Substances Data)

Usage

General Description

(tet-Butoxycarbonyl)oxycefcapene pivoxil is a chemical compound that belongs to the class of cephalosporin antibiotics. It is commonly used as a prodrug form of cefcapene, which means that it is metabolized in the body to produce the active form of the antibiotic. (tert-Butoxycarbonyl)oxycefcapene pivoxil is used to treat a variety of bacterial infections, particularly those caused by Gram-positive and Gram-negative bacteria. It works by inhibiting the synthesis of the bacteria's cell wall, leading to their eventual death. (tert-Butoxycarbonyl)oxycefcapene pivoxil is available in oral tablet form, making it convenient for patients to take at home to manage their infections. It is considered to be effective and generally well-tolerated in patients.

InChI:InChI=1/C28H37N5O10S2/c1-8-9-15(16-12-45-25(30-16)32-26(39)43-28(5,6)7)19(34)31-17-20(35)33-18(14(10-40-24(29)38)11-44-21(17)33)22(36)41-13-42-23(37)27(2,3)4/h9,12,17,21H,8,10-11,13H2,1-7H3,(H2,29,38)(H,31,34)(H,30,32,39)/b15-9-/t17-,21-/m1/s1

Upstream product

• 53064-79-2 iodomethyl pivaloate 
• 105890-10-6 7β-<(Z)-2-(2-tert-butoxycarbonylaminothiazol-4-yl)-2-pentenoylamino>-3-carbamoyloxymethyl-3-cephem-4-carboxylic acid 
• 107185-27-3 7β-<(Z)-2-(2-tert-butoxycarbonylaminothiazol-4-yl)-2-pentenoylamino>-3-acetoxymethyl-3-cephem-4-carboxylic acid 
• 153012-24-9 C₁₄H₂₀N₂O₆S₂ 
• 957-68-6 7-Aminocephalosporanic acid 
• 15690-38-7 (6R,7R)-7-amino-3-hydroxymethyl-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid 
• 153012-37-4 [(6R,7R)-7-[(2Z)-2-(2-{[(tert-butoxy)carbonyl]amino}-1,3-thiazol-4-yl)pent-2-enamido]-3-[(carbamoyloxy)methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carbonyloxy]methyl 2,2-dimethylpropanoate salt 
• 1360188-88-0 C₂₁H₂₄N₄O₆S₂ 
• 153012-25-0 (6R,7R)-7-((2Z)-2-(2-tert-butoxycarbonylaminothiazol-4-yl)-2-pentenoyl)amino-3-hydroxymethyl-3-cephem-4-carboxylic acid 
• 147816-25-9 Boc-cefcapene sodium 
• 86978-24-7 (Z)-2-[2-(tert-butoxycarbonylamino)thiazol-4-yl]pent-2-enoic acid 
• 105890-09-3 diphenylmethyl 7β-<(Z)-2-(2-tert-butoxycarbonylaminothiazol-4-yl)-2-pentenoylamino>-3-carbamoyloxymethyl-3-cephem-4-carboxylate 

Downstream Products

• 105889-45-0 cefcapene pivoxil 

Relevant articles and documents

Hydrochloric acid Cefcapene pivoxil preparation method

The invention discloses a preparation method of cefcapene pivoxil hydrochloride. The preparation method comprises the following steps: 1), a compound shown in the formula I is stirred and dissolved in pyridine, methanesulfonyl chloride is added and stirred for reaction, filtering is performed, and a liquid containing a compound shown in the formula II is obtained; 2), 7-ACA reacts with the liquid containing the compound shown in the formula II in the presence of proline and diisopropylamine, and a compound shown in the formula III is obtained; 3), the compound shown in the formula III reacts with potassium carbonate, and a compound shown in the formula IV is obtained; 4), the compound shown in the formula IV reacts with chlorosulfonyl isocyanate in the presence of diisopropylamine, and a compound shown in the formula V is obtained; 5), the compound shown in the formula V and obtained in the step 4) reacts with iodomethyl pivalate in DMF (dimethyl formamide) in the presence of potassium phosphate and copper acetate, a phosphate solution is added to end the reaction, and a compound shown in the formula VI is obtained; 6), cefcapene pivoxil hydrochloride is obtained after deprotection of the compound shown in the formula VI. The method increases product yield greatly and is particularly suitable for mass production, and few by-products are produced.

A practical synthesis of cefcapene pivoxil

Cefcapene pivoxil monohydrochloride monohydrate, a broad spectrum third-generation cephalosporin for oral administration, was prepared by reacting three centers of 7-amino-3-(hydroxymethyl)cephalosporinic acid (7-HACA), derived from 7-aminocephalosporanic acid. The coupling of 7-HACA and (Z)-2-[2-(Boc-amino)thiazol-4-yl]pent-2-enoic acid, followed by carbamylation with chlorosulfonyl isocyanate, and precipitation with diisopropylamine gave the key intermediate, in which thiazole side chain and carbamoyl group had been introduced into the 7-amino and 3-hydroxymethyl groups of 7-HACA, respectively, in a continuous procedure. Afterwards, the intermediate was esterified with pivaloyloxymethyl iodide to complete the modification of the C4 carboxy group affording Boc-cefcapene pivoxil, from which the desired product was finally obtained by an economical Boc removal and successive formation of the hydrochloride in 36% overall yield on a decagram scale. This synthesis promises an easy entry to cefcapene pivoxil monohydrochloride monohydrate with convenient manipulation, simple isolation, and good yields; it is of potential value for production on an industrial scale. Georg Thieme Verlag Stuttgart · New York.

Synthesis and structure-activity relationships of 7β-[(Z)-2-(2-aminothiazol-4-yl)-3-(substituted)-2- propenoyl-amino]-3-cephems with C-3 substitutions

Synthesis and biological activity of a series of 7β-[(Z)-2-(2-aminothiazol-4-yl)-3-(substituted)-2- propenoylamino]-3-cephem-4-carboxylic acids with C-3 substitutions and their pivaloyloxymethyl esters are described. These acid compounds exhibited potent antibacterial activity against both Gram-positive and Gram-negative bacteria. Pivaloyloxymethyl esters of selected compounds in this series were found to be well absorbed from small intestine in mice. Pivaloyloxymethyl 7β-[(Z)-2-(2-aminothiazol-4-yl)-2-pentenoylamino]-3- carbamoyloxymethyl-3-cephem-4-carboxyiate hydrochloride hydrate (S-1108) was finally selected as the candidate for clinical evaluation.