86978-24-7

Usage

Chemical Properties

White Solid

Uses

Different sources of media describe the Uses of 86978-24-7 differently. You can refer to the following data:
1. Intermediate for Cefcapene
2. Cefcapene intermediate.

InChI:InChI=1/C13H18N2O4S/c1-5-6-8(10(16)17)9-7-20-11(14-9)15-12(18)19-13(2,3)4/h6-7H,5H2,1-4H3,(H,16,17)(H,14,15,18)/b8-6-

Upstream product

• 24424-99-5 di-tert-butyl dicarbonate 
• 916597-44-9 ethyl 2-(2-bromoacetyl)pent-2-enoate 
• 1026906-47-7 2-(2-tert-Butoxycarbonylamino-thiazol-4-yl)-3-tert-butoxycarbonyloxy-pentanoic acid ethyl ester 
• 86978-09-8 tert-butyl (2E)-2-[(tert-butoxycarbonyl)inimo]-4-(2-ethoxy-2-oxoethyl)-1,3-thiazole-3-(2H)-carboxylate 
• 158743-37-4 2-(2-tert-butoxycarbonylaminothiazol-4-yl)-2-pentenoic acid ethyl ester 

Downstream Products

• 158497-27-9 diphenylmethyl 7β-<(Z)-2-(2-tert-butoxycarbonylaminothiazol-4-yl)-2-pentenoylamino>-3-acetoxymethyl-3-cephem-4-carboxylate 
• 158497-34-8 diphenylmethyl 7β-<(Z)-2-(2-tert-butoxycarbonylaminothiazol-4-yl)-2-pentenoylamino>-3-(2-methyl-1,3,4-thiadiazol-5-ylthio)methyl-3-cephem-4-carboxylate 
• 105889-45-0 cefcapene pivoxil 
• 105889-80-3 ((6R,7R)-3-((aminocarbonyl)oxy)methyl-7-((Z)-2-(2-tert-butoxycarbonylaminothiazol-4-yl)-2-pentenoyl)amino)-8-oxo-5-thio-1-azabicyclo[4.2.0]-oct-2-ene-2-carboxylic acid(2,2-dimethyloxypropoxymethyl)ester 
• 135889-00-8 cefcapene 
• 105890-09-3 diphenylmethyl 7β-<(Z)-2-(2-tert-butoxycarbonylaminothiazol-4-yl)-2-pentenoylamino>-3-carbamoyloxymethyl-3-cephem-4-carboxylate 
• 158497-31-5 diphenylmethyl 7β-<(Z)-2-(2-tert-butoxycarbonylaminothiazol-4-yl)-2-pentenoylamino>-3-methoxymethyl-3-cephem-4-carboxylate 
• 158497-28-0 diphenylmethyl 7β-<(Z)-2-(2-tert-butoxycarbonylaminothiazol-4-yl)-2-pentenoylamino>-3-chloro-3-cephem-4-carboxylate 

Relevant academic research and scientific papers

Method for preparing cefcapene side chain acid

The invention relates to a method for preparing cefcapene side chain acid, and belongs to the technical field of refined medical intermediates. The method comprises the following steps: adding ketene dimer into an alcohol organic solvent in the presence of nitrogen, dropwise adding bromine for reaction, adding a mixed liquid of dichloromethane and water for quenching reaction, separating an organic phase, adding acetic acid into the organic phase, dropwise adding propyl aldehyde and an organic alkali catalyst A for reaction, then adding thiourea for reaction, performing vacuum distillation for concentration, adding dichloromethane, di-tert-butyl dicarbonate ester and an organic alkali catalyst B into a concentrated solution for reaction, adding a caustic soda liquid for reaction, cooling, dropwise adding hydrochloric acid for crystallization, filtering, performing drip washing with an isopropanol solution, and drying, thereby obtaining (Z)-2-(2-t-butyloxycarboryl aminothiazole-4-yl)-2-pentenoic acid, that is, the cefcapene side chain acid. As the ketene dimer is adopted as an initial raw material, the method is small in side reaction, high in yield, high in purity of obtained products and gentle in reaction condition, and industrial production can be relatively easily achieved.

A head spore card side chain acid method for the preparation of

The invention discloses a preparation method of BTPA ((Z)-2-(2-tert-butoxycarbonyl amino-thiazol-4-yl)-2-pentenoic acid). The method comprises the steps that by taking D301 type weak-base ion-exchange resin in Formula (II) as shown in the specification and metal oxide as a composite catalyst, and dichloromethane as a solvent, bromo acetylacetic ester, propionaldehyde, thiourea and di-tert-butyl dicarbonate ester undergo a one pot reaction at 0-30 DEG C for 1-10h; 2-(2-tert-butoxycarbonyl amino-thiazol-4-yl)-2-pentenoic acid ethyl ester in Formula (III) as shown in the specification is generated; the composite catalyst and the solvent are then removed; and hydrolysis is performed; and BTPA in Formula (I) as shown in the specification is obtained. Metal oxide is one of, a mixture of random two of, or a mixture of the three of magnesium oxide, aluminium oxide or calcium oxide; R1 and R2 in Formula (II) are independent methyl or hydrogen atom respectively; and n is a polymerization degree.

Stereoselective or exclusive synthesis of ethyl (Z)-2-(2-substituted- thiazol-4-yl)pent-2-enoates from ethyl (E/Z)-2-(2-bromoacetyl)pent-2-enoate

A stereoselective or exclusive approach to a series of ethyl (Z)-2-(2-substituted-thiazol-4-yl)pent-2-enoates from ethyl (E/Z)-2-(2- bromoacetyl)pent-2-enoate and thioureas or thioamides was reported in good yields. This approach involves a quaternary carbon stereocontrolled cis-configuration formation, and opportunely blocking a potential E/Z isomerization. The practical applicability was highlighted by the synthesis of (Z)-2-(2-tert-butoxycarbonylaminothiazol-4-yl)pent-2-enoic acid, a commercially important side-chain material of cefcapene pivoxil, in a two-step procedure. 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-desacetoxymethylcephalosporins

Synthesis and biological activity of a series of 7β-[(Z)-2-(2-aminothiazol-4-yl)-3-(substituted)-2- propenoylamino]-3-cephem-4-carboxylic acids 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.