86978-24-7

Basic information

• Product Name: (Z)-2-(2-tert-Butoxycarbonylaminothiazol-4-yl)-2-pentenoic acid
• Synonyms: 2-[(2-AMINO-THIAZOL-4-YL)-ETHOXYCARBONYL-METHYLENEAMINOOXY]-2-METHYL-PROPIONIC ACID TERT-BUTYL ESTER;EATB;ETHYL (Z)-2-(2-AMINOTHIAZOL-4-YL)-2-(1-T-BUTOXYCARBONYL-1-METHYL)ETHOXYIMINOACETATE;BTPA;LABOTEST-BB LT00441039;(Z)-2-(2-T-BUTOXYCARBONYLAMINOTHIAZOL-4-YL)-2-PENTENOIC ACID;(z)-2-(2-tert-butoxycarbonylaminothiazol-4-yl)-2-pentenoic acid;BTPA:( Z )-2-(2-T-BUTOXYCARBONYLAMINOTHIAZOL-4-YL)-2-PENTENOIC ACID
• CAS NO: 86978-24-7
• Molecular Formula: C13H18N2O4S
• Molecular Weight: 298.36
• EINECS: 430-100-3
• Product Categories: Heterocycles;Intermediates & Fine Chemicals;Pharmaceuticals;Sulfur & Selenium Compounds
• Mol File: 86978-24-7.mol
• Article Data: 4

Chemical Properties

• Melting Point: 159-161°C
• Appearance: white solid
• Density: 1.279 g/cm³
• Refractive Index: 1.583
• Storage Temp.: Refrigerator
• Solubility: Chloroform, Iso-propanol
• PKA: 3.34±0.36(Predicted)
• CAS DataBase Reference: (Z)-2-(2-tert-Butoxycarbonylaminothiazol-4-yl)-2-pentenoic acid(CAS DataBase Reference)
• NIST Chemistry Reference: (Z)-2-(2-tert-Butoxycarbonylaminothiazol-4-yl)-2-pentenoic acid(86978-24-7)
• EPA Substance Registry System: (Z)-2-(2-tert-Butoxycarbonylaminothiazol-4-yl)-2-pentenoic acid(86978-24-7)

Safety Data

• Hazardous Substances Data: 86978-24-7(Hazardous Substances Data)

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 
• 158497-28-0 diphenylmethyl 7β-<(Z)-2-(2-tert-butoxycarbonylaminothiazol-4-yl)-2-pentenoylamino>-3-chloro-3-cephem-4-carboxylate 
• 158497-31-5 diphenylmethyl 7β-<(Z)-2-(2-tert-butoxycarbonylaminothiazol-4-yl)-2-pentenoylamino>-3-methoxymethyl-3-cephem-4-carboxylate 
• 105890-09-3 diphenylmethyl 7β-<(Z)-2-(2-tert-butoxycarbonylaminothiazol-4-yl)-2-pentenoylamino>-3-carbamoyloxymethyl-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 
• 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 

Relevant articles and documents

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.

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.