127199-45-5

Basic information

• Product Name: Carbamic acid, (7S)-5-azaspiro[2.4]hept-7-yl-, 1,1-dimethylethyl ester (9CI)
• Synonyms: Carbamic acid, (7S)-5-azaspiro[2.4]hept-7-yl-, 1,1-dimethylethyl ester (9CI);(S)-7-N-BOC-AMINO-5-AZA-SPIRO[2.4]HEPTANE;(S)-tert-butyl 5-azaspiro[2.4]heptan-7-ylcarbamate;(7S)-5-Azaspiro[2.4]hept-7-ylcarbamic acid tert-butyl ester;(S)-7-tert-Butoxycarbonylamino-5-azaspiro[2.4]heptane;CarbaMic acid, N-(7S)-5-azaspiro[2.4]hept-7-yl-, 1,1-diMethylethyl ester;tert-butyl N-[(7S)-5-azaspiro[2.4]heptan-7-yl]carbaMate;(S)-(5-Aza-spiro[2.4]hept-7-yl)-carbamic acid tert-butyl ester
• CAS NO: 127199-45-5
• Molecular Formula: C₁₁H₂₀N₂O₂
• Molecular Weight: 212.2887
• EINECS: 1312995-182-4
• Product Categories: N-BOC
• Mol File: 127199-45-5.mol

Chemical Properties

• Boiling Point: 329.029ºC at 760 mmHg
• Flash Point: 152.791ºC
• Appearance: /
• Density: 1.099g/cm3
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.513
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• PKA: 12.39±0.40(Predicted)
• CAS DataBase Reference: Carbamic acid, (7S)-5-azaspiro[2.4]hept-7-yl-, 1,1-dimethylethyl ester (9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: Carbamic acid, (7S)-5-azaspiro[2.4]hept-7-yl-, 1,1-dimethylethyl ester (9CI)(127199-45-5)
• EPA Substance Registry System: Carbamic acid, (7S)-5-azaspiro[2.4]hept-7-yl-, 1,1-dimethylethyl ester (9CI)(127199-45-5)

Safety Data

• Hazardous Substances Data: 127199-45-5(Hazardous Substances Data)

Usage

InChI:InChI=1/C11H20N2O2/c1-10(2,3)15-9(14)13-8-6-12-7-11(8)4-5-11/h8,12H,4-7H2,1-3H3,(H,13,14)/t8-/m1/s1

Upstream product

• 127199-42-2 7(S)-<(tert-butoxycarbonyl)amino>-5-<1(R)-phenylethyl>-5-azaspiro<2.4>heptane 
• 24424-99-5 di-tert-butyl dicarbonate 
• 180506-32-5 (R)-5-Benzyl-7-hydroxy-5-aza-spiro[2.4]heptan-4-one 
• 144282-41-7 (S)-7-amino-5-benzyl-5-azaspiro[2.4]heptan-4-one 
• 129306-04-3 5-benzyl-5-azaspiro[2.4]heptane-4,7-dione 
• 220969-69-7 1-(2-Benzylamino-acetyl)-cyclopropanecarboxylic acid ethyl ester 
• 207554-17-4 1-[2-(Benzyl-tert-butoxycarbonyl-amino)-acetyl]-cyclopropanecarboxylic acid ethyl ester 
• 58632-95-4 2-(tert-Butoxycarbonyloxyimino)-2-phenylacetonitrile 
• 127199-41-1 7-(S)-amino-5-<1(R)-phenylethyl>-5-azaspiro<2.4>heptane 
• 127199-38-6 7-(S)-amino-5-<1(R)-phenylethyl>-4-oxo-5-azaspiro<2.4>heptane 
• 127199-37-5 4,7-dioxo-5-<1(R)-phenylethyl>-5-azaspiro<2.4>heptane 
• 32933-03-2 ethyl 1-acetylcyclopropanecarboxylate 
• 129306-05-4 ethyl 1-(2-bromoacetyl)cyclopropanecarboxylate 
• 1432056-70-6 5-benzyl-7(S)-tert-butoxycarbonylamino-5-azaspiro[2,4]heptane 

Downstream Products

• 127199-06-8 7-((S)-7-Amino-5-aza-spiro[2.4]hept-5-yl)-8-chloro-6-fluoro-1-(2-fluoro-cyclopropyl)-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid 
• 127254-12-0 sitafloxacin 
• 127199-06-8 7-((S)-7-Amino-5-aza-spiro[2.4]hept-5-yl)-8-chloro-6-fluoro-1-((1S,2R)-2-fluoro-cyclopropyl)-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid 
• 627532-31-4 ethyl 4-[7-(S)-tert-butoxycarbonylamino-5-azaspiro[2.4]hept-5-yl]-2,5-difluoro-3-methoxybenzoylacetate 

Relevant articles and documents

Preparation method of sitafloxacin hydrate

The invention discloses a preparation method of sitafloxacin hydrate. The method comprises the following steps: taking ethyl 4-bromoacetoacetate used as a raw material, enabling ethyl 4-bromoacetoacetate to be fully reacted with 1,2-dibromoethane and preparing the obtained product into a compound II in the presence of carbonyl reduction enzyme; taking the compound II, enabling the compound II to carry out cyclization reaction with benzylamine in a solvent in the presence of cesium carbonate, enabling the obtained product to be reacted with DPPA and preparing a compound IV; reducing nitrine group of the compound IV to prepare a compound V; connecting primary amine group of the compound V with a BOC protection group to obtain a compound VI; reducing the compound VI through Pd/C, enabling theobtained product to be reacted with 8-chlorine-6,7-difluoro-1-[(1R,2s)-2-fluorocyclopropyl]-4-oxo-1,4-dihydroquinoline-3-carboxylic acid ethyl ester to prepare a compound VIII; and carrying out deprotection of the compound VIII to obtain sitafloxacin hydrate. The sitafloxacin hydrate is few in preparation steps, simple in post-treatment and relatively high in yield.

Method for (7S)-5- synthesizing [2.4] tert -7-butyl carbamic acid tert-butyl (by machine translation)

To the preparation method disclosed by the invention (7S) - 5 - [2.4] the raw materials are easily available, the process is simple, the (>99.0% ee) optical purity of the obtained product is high, and the method is suitable for industrial large-scale production. The invention provides a novel method for synthesizing a spirocyclic intermediate of sitafloxacin. (by machine translation)

Preparation method of sitafloxacin key intermediate

The invention discloses a preparation method of a sitafloxacin key intermediate, namely a preparation method of (7S)-t-butyloxycarboryl amino-5-azaspiro[2,4] heptane. By taking (7S)-t-butyloxycarborylamino-5-N-benzyl azaspiro[2,4] heptane as a raw material, the (7S)-t-butyloxycarboryl amino-5-azaspiro[2,4] heptane is obtained by means of devitrification after a reaction by taking palladium carbonas a catalyst and ammonium formate as a hydrogen source in an alcohol solvent. The method is simple to operate and mild in reaction, solves the problem that the triatomic ring on the spiral ring is opened successively, and meanwhile, can obtain the sitafloxacin key intermediate which is high in purity. The sitafloxacin obtained by the follow-up process is few in impurity, high in purity and suitable for the demand on industrial production.

Preparation method of sitafloxacin hydrate five-membered ring side chain intermediate

The invention relates to a preparation method of a sitafloxacin hydrate five-membered ring side chain intermediate. The preparation method comprises following steps: keto carbonyl groups of a raw material 1 are reacted with sodium cyanoborohydride or sodium triacetoxyborohydride in the presence of ammonium acetate or ammonium chloride; reduction of amide carbonyl groups of an obtained production is realized with lithium aluminum hydride; free amino groups of a reduction product are reacted with di-tert-butyl dicarbonate ester in the presence of an alkali; phenethyl groups of an obtained compound are subjected to reductive destruction with formic acid or a formate in the presence of palladium-carbon so as to obtain the sitafloxacin hydrate intermediate (product 5). Reaction conditions of the preparation method are mild; equipment requirements are low; preparation process is safe; stereoselectivity is excellent; the raw material reagents are cheap and easily available; and production cost is low.

Processes for preparation of bicyclic compounds and intermediates therefor

A process for preparing intermediate compound (VII), compound (VIII) and compound (XIV) which will be raw materials for the synthesis of a synthetic antibactrial compound, via compound (I) or compound (X) and then, compound (II), the compounds each being shown below; and novel compounds useful for the preparation.

PROCESSES FOR PREPARATION OF BICYCLIC COMPOUNDS AND INTERMEDIATES THEREFOR

A process for preparing intermediate compound (VII), compound (VIII) and compound (XIV) which will be raw materials for the synthesis of a synthetic antibactrial compound, via compound (I) or compound (X) and then, compound (II), the compounds each being shown below; and novel compounds useful for the preparation.

Pyridone antibiotic with improved safety profile

Antibacterial compounds having the formula STR1 and the pharmaceutically acceptable salts, esters and amides thereof, as well as pharmaceutical compositions containing such compounds and the use of the same in the treatment of bacterial infections.

An efficient synthesis of a key intermediate of DU-6859a via asymmetric microbial reduction

An efficient synthetic method for the C-7 substituent of DU-6859a (1), which is a new-generation antibacterial quinolone carboxylic acid, was established by utilizing an enantioselective microbial reduction of 5- benzyl-4,7-dioxo-5-azaspiro[2,4]heptane (7) to the corresponding chiral alcohol (8) as the key reaction. This synthetic method was based on use of AIPHOS (Artificial Intelligence for Planning and Handling Organic Synthesis), which is a synthesis design system that generates suitable retrosynthetic routes from the standpoints of both novelty and practicality.

(Fluorocyclopropyl)quinolones. 2. Synthesis and stereochemical structure- activity relationships of chiral 7-(7-amino-5-azaspiro[2.4]heptan-5-yl)-1- (2-fluorocyclopropyl)quinolone antibacterial agents

A series of novel chiral 7-(7-amino-5-azaspiro[2.4]heptan-5-yl)-8-chloro- 1-(2-fluorocyclopropyl)-quinolones were synthesized as a continuation of a research project of 1-(2-fluorocyclopropyl)-quinolones by considering stereochemical and physicochemical properties of the molecule. Absolute configurations of the 1-(cis-2-fluorocyclopropyl) moiety and the 7-(7-amino- 5-azaspiro-[2.4]heptan-5-yl) moiety were determined by X-ray crystallographic analysis. Stereochemical structure-activity relationship studies indicated that 1-[(1R,2S)-2-fluorocyclopropyl] and 7-[(7S)-amino-5-azaspiro[2.4]heptan- 5-yl] derivatives are more potent against Gram-positive and Gram-negative bacteria than the other stereoisomers and 7-[(7S)-7-amino-5-azaspiro[2.4]- heptan-5-yl]-8-chloro-1-[(1R,2S)-2-fluorocyclopropyl]quinolone (33) is the most potent of all stereoisomers. Pharmacokinetic profiles and physicochemical properties of the selected compounds were also examined, and it was found that 33 (DU-6859a) possesses moderate lipophilicity and good pharmacokinetic profiles.