877674-77-6

Basic information

• Product Name: 7-Chloro-2-[[[(1S)-2,2-dimethylcyclopropyl]carbonyl]amino]-2-heptenoic acid
• Synonyms: 7-Chloro-2-[[[(1S)-2,2-dimethylcyclopropyl]carbonyl]amino]-2-heptenoic acid;(2Z)-7-chloro-2-[[[(1S)-2,2-dimethylcyclopropyl]carbonyl]amino]-2-Heptenoic acid;(E)-7-chloro-2-[[(1S)-2,2-dimethylcyclopropanecarbonyl]amino]hept-2-enoic acid
• CAS NO: 877674-77-6
• Molecular Formula: C₁₃H₂₀ClNO₃
• Molecular Weight: 273.7558
• EINECS: 1308068-626-2
• Mol File: 877674-77-6.mol
• Article Data: 7

Chemical Properties

• Boiling Point: 504.547 °C at 760 mmHg
• Flash Point: 258.941 °C
• Appearance: /
• Density: 1.189
• Storage Temp.: Hygroscopic, -20°C Freezer, Under inert atmosphere
• Solubility: DMSO (Slightly), Methanol (Slightly)
• Stability: Hygroscopic
• CAS DataBase Reference: 7-Chloro-2-[[[(1S)-2,2-dimethylcyclopropyl]carbonyl]amino]-2-heptenoic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 7-Chloro-2-[[[(1S)-2,2-dimethylcyclopropyl]carbonyl]amino]-2-heptenoic acid(877674-77-6)
• EPA Substance Registry System: 7-Chloro-2-[[[(1S)-2,2-dimethylcyclopropyl]carbonyl]amino]-2-heptenoic acid(877674-77-6)

Safety Data

• Hazardous Substances Data: 877674-77-6(Hazardous Substances Data)

Usage

Uses

(2Z)?-7-?Chloro-?2-?[[[(1S)?-?2,?2-?dimethylcyclopropyl]?carbonyl]?amino]?-?2-?heptenoic Acid is a reagent used in the preparation of Cilastatin (C441105), prevents renal metabolism of penem and carbapenem antibiotics by specific and reversible dehydropeptidase I inhibition. Antibacterial adjunct.

Upstream product

• 78834-75-0 ethyl-7-Chloro-2-oxoheptanoate 
• 75885-58-4 (S)-2,2-dimethylcyclopropanecarboxamide 
• 166037-21-4 (E)-7-chloro-2[[(1S)-2,2-dimethyl cyclopropane]carboxamide]-2-heptenoic acid 
• 1022895-92-6 ethyl 7-chloro-2-{[(1S)-2,2-dimethylcyclopropyl]formamido}hept-2-enoate 
• 877758-94-6 (Z)-7-chloro-2-((S)-2,2-dimethylcyclopropanecarboxamido)-2-heptenoic acid ethyl ester 

Downstream Products

• 82009-34-5 cilastatine 

Relevant articles and documents

Cilastatin sodium intermediate preparation method

The invention belongs to the technical field of medicines, and particularly provides a cilastatin sodium intermediate preparation method, which comprises: simply preparing a (Z)-7-X-2((2s)-2,2-dimethylcyclopropaneformamido)-2-heptenoic acid crude product through a one-pot method by using 7-X-2-oxoheptanoic acid ethyl ester and (s)-2,2-dimethylcyclopropaneformamide as raw materials sequentially under the action of a catalyst, concentrated hydrochloric acid and hydrogen chloride gas, and re-crystallizing to prepare a (Z)-7-X-2((2s)-2,2-dimethylcyclopropaneformamido)-2-heptenoic acid refined product. According to the invention, the method has advantages of short synthetic route, simple operation and high product purity, and is suitableness for industrial production.

Purification method of ethyl 7-chloro-2-oxoheptanoate

The invention provides a purification method of ethyl 7-chloro-2-oxoheptanoate, wherein the purification method comprises the steps: firstly, carrying out a reaction of ethyl 7-chloro-2-oxoheptanoate oil crude product and a hydrosulphite solution, and separating to obtain a sulfite solid of ethyl 7-chloro-2-oxoheptanoate; then, dissolving the sulfite solid of ethyl 7-chloro-2-oxoheptanoate in water, adding an acid or alkali at a certain temperature, and decomposing the sulfite of ethyl 7-chloro-2-oxoheptanoate into ethyl 7-chloro-2-oxoheptanoate; and finally, extracting with an organic solvent immiscible with water, to obtain ethyl 7-chloro-2-oxoheptanoate having the purity improved. The method is simple in operation and suitable for industrialized production, and ensures the purity of a subsequent product and final product cilastatin sodium.

Process for the Preparation of Cilastatin and Sodium Salt

The present invention relates to an improved process for the preparation of Cilastatin Sodium of formula (I). The present invention also provides an isolation technique for Cilastatin acid from the reaction mixture.