175463-32-8

Basic information

• Product Name: 1-Boc-3-cyano-4-oxopyrrolidine
• Synonyms: TERT-BUTYL-3-CYANO-4-OXOPYRROLIDINE-1-CARBOXYLATE;N-BOC-3-CYANO-4-PYRROLIDINONE;3-CYANO-4-OXO-PYRROLIDINE-1-CARBOXYLIC ACID TERT-BUTYL ESTER;4-CYANO-1-N-BOC PYRROLIDIN-3-ONE;1-BOC-3-CYANO-4-OXOPYRROLIDINE;1-N-BOC-3-CYANO-PYRROLID-4-ONE;1-N-BOC-3-CYANO-PYRROLIDINONE-4;1-N-BOC-3-CYANO-PYRROLIDONE-4
• CAS NO: 175463-32-8
• Molecular Formula: C₁₀H₁₄N₂O₃
• Molecular Weight: 210.23
• EINECS: 1533716-785-6
• Product Categories: pharmacetical;Pyrrole&Pyrrolidine&Pyrroline
• Mol File: 175463-32-8.mol
• Article Data: 12

Chemical Properties

• Melting Point: 160-167°C
• Boiling Point: 360.738 °C at 760 mmHg
• Flash Point: 171.968 °C
• Appearance: /
• Density: 1.187 g/cm³
• Vapor Pressure: 2.17E-05mmHg at 25°C
• Refractive Index: 1.499
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• PKA: -4.24±0.40(Predicted)
• CAS DataBase Reference: 1-Boc-3-cyano-4-oxopyrrolidine(CAS DataBase Reference)
• NIST Chemistry Reference: 1-Boc-3-cyano-4-oxopyrrolidine(175463-32-8)
• EPA Substance Registry System: 1-Boc-3-cyano-4-oxopyrrolidine(175463-32-8)

Safety Data

• Statements: 20/21/22-36/37/38
• Safety Statements: 9-26-36/37
• RIDADR: UN3439
• HazardClass: 6.1
• PackingGroup: III
• Hazardous Substances Data: 175463-32-8(Hazardous Substances Data)

Usage

Description

1-Boc-3-cyano-4-oxopyrrolidine, also known as 1-Boc-3-cyano-4-pyrrolidinone, is a light yellow powder with unique chemical properties. It is an important intermediate compound in the synthesis of various pharmaceuticals and organic compounds.

Uses

1. Used in Pharmaceutical Synthesis:
1-Boc-3-cyano-4-oxopyrrolidine is used as a key intermediate in the synthesis of new napthyridone antibacterials. These antibacterials are essential for developing novel treatments against resistant bacterial strains, contributing to the fight against antibiotic resistance.
2. Used in the Synthesis of Gemifloxacin Derivatives:
1-Boc-3-cyano-4-oxopyrrolidine is also utilized in the synthesis of gemifloxacin derivatives containing a benzyloxime moiety. Gemifloxacin is a fluoroquinolone antibiotic used to treat various bacterial infections. The development of novel gemifloxacin derivatives with improved properties, such as enhanced efficacy or reduced side effects, is crucial for addressing the challenges posed by antibiotic resistance.
3. Used in the Chemical Industry:
In the chemical industry, 1-Boc-3-cyano-4-oxopyrrolidine can be employed as a building block for the synthesis of various organic compounds, including pharmaceuticals, agrochemicals, and other specialty chemicals. Its unique structure and reactivity make it a valuable asset in the development of new molecules with potential applications in various fields.

InChI:InChI=1/C10H14N2O3/c1-10(2,3)15-9(14)12-5-7(4-11)8(13)6-12/h7H,5-6H2,1-3H3

Upstream product

• 266353-18-8 N-tert-butoxycarbonyl-2-(2-cyanoethyl)aminoacetic acid ethyl ester 
• 44981-94-4 N-cyanoethyl glycine ethyl ester 
• 24424-99-5 di-tert-butyl dicarbonate 
• 266353-19-9 [tert-butoxycarbonyl-(2-cyanoethyl)amino]acetic acid methyl ester 
• 3088-42-4 N-(2-cyanoethyl)glycine 
• 44915-39-1 [(2-cyanoethyl)amino]acetic acid methyl ester 

Downstream Products

• 197143-33-2 tert-butyl 3-cyano-4-hydroxypyrrolidine-1-carboxylate 
• 398491-59-3 3-amino-4,6-dihydro-1H-pyrrolo[3,4-c]pyrazole-5-carboxylic acid tert-butyl ester 
• 398495-65-3 3-amino-4,6-dihydro-pyrrolo[3,4-c]pyrazole-1,5-dicarboxylic acid 5-tert-butyl ester 1-ethyl ester 
• 761443-69-0 5-tert-butyl 1-ethyl 3-{[4-(4-methylpiperazin-1-yl)benzoyl]amino}-4,6-dihydropyrrolo[3,4-c]pyrazole-1,5-dicarboxylate 
• 850997-37-4 ethyl 5-(2,6-diethylphenylcarbamoyl)-3-[4-(4-methylpiperazin-1-yl)benzoylamino]-5,6-dihydro-4H-pyrrolo[3,4-c]pyrazole-1-carboxylate 
• 773826-73-6 tert-butyl 3-(aminomethyl)-4-hydroxypyrrolidine-1-carboxylate 
• 175463-34-0 4-(tert-butoxycarbonyl)aminomethyl-1-(t-butoxycarbonyl)pyrrolidin-3-ol 
• 175463-14-6 gemifloxacin 
• 398491-59-3 3-amino-2,6-dihydro-4H-pyrrolo[3,4-c]pyrazole-5-carboxylic acid tert-butyl ester 
• 1227461-24-6 4-cyano-3-amino-1-(N-tert-butoxycarbonyl)-3,4-pyrroline 
• 1251754-64-9 7-(2-methyl-3-aminopyrrolo[3,4-c]pyrazol-5(2H,4H,6H)-yl)-1-(2,4-difluorophenyl)-6-fluoro-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylic acid 
• 175463-36-2 tert-butyl 3-(tert-butoxycarbonyl)aminomethyl-4-(hydroxyimino)pyrrolidine-1-carboxylate 
• 1357948-74-3 5-(3-methoxy-phenyl)-7-oxo-1,3,6,7-tetrahydro-8-thia-2,4,6-triaza-cyclopenta[a]indene-2-carboxylic acid ethyl ester 
• 1357948-76-5 5-(3-methoxy-phenyl)-7-morpholin-4-yl-1,3-dihydro-8-thia-2,4,6-triaza-cyclopenta[a]indene-2-carboxylic acid ethyl ester 

Relevant articles and documents

Synthesis and in-vitro antibacterial activity of 7-(3-aminopyrrolo[3,4-c] pyrazol-5(2H,4H,6H)-yl)-6-fluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid derivatives

A series of novel 7-(3-aminopyrrolo[3,4-c]pyrazol-5(2H,4H,6H)-yl)-6-fluoro- 4-oxo-1,4-dihydroquinoline-3-carboxylic acid derivatives was designed, synthesized and characterized by 1H-NMR, MS and HRMS. These fluoroquinolones were evaluated for their in-vitro antibacterial activity against representative Gram-positive and Gram-negative strains. Generally, all of the target compounds display rather weak potency against the tested Gram-negative strains, but most of them exhibit good potency in inhibiting the growth of S. aureus including methicillin-resistant Staphylococcus aureus (MRSA) and Staphylococcus epidermidis including methicillin-resistant S. epidermidis (MRSE) (MIC: 0.125-8 μg/mL). In particular, the compound 9g is 2 to 32 fold more potent than gemifloxacin (GM), moxifloxacin (MX), gatifloxacin (GT), and levofloxacin (LV) against S. pneumoniae 08-3, K. pneumoniae 09-23, and P. aeruginosa ATCC27853, 4 to 32 fold more potent than MX, GM, and LV against K. pneumoniae 09-21, and more active than or comparable to the four reference drugs against P. aeruginosa 09-32. A series of novel fluoroquinolone derivatives was designed and synthesized. All target compounds display rather weak potency against the tested Gram-negative strains, but most of them exhibit good potency in inhibiting the growth of Staphylococcus aureus and Staphylococcus epidermidis. In particular, the compound 9g is the most promising drug.

A preparation method of the lucky mischa star side chain

The invention relates to a preparation method of a gemifloxacin side chain. The preparation method comprises that N-tertbutyloxycarbonyl-4-cyano-3-pyrrolidone is prepared or taken and then reacts with trimethyl orthoformate to produce N-tertbutyloxycarbonyl-4-cyano-3-dimethoxypyrrolidone, the N-tertbutyloxycarbonyl-4-cyano-3-dimethoxypyrrolidone, methanol, a catalyst and (BOC)2 anhydride undergo a complete reaction at a room temperature to produce N-tertbutyloxycarbonyl-4-aminomethyl-3-dimethoxypyrrolidone, the N-tertbutyloxycarbonyl-4-aminomethyl-3-dimethoxypyrrolidone and HAC undergo a complete reaction at a room temperature with stirring to produce N-tertbutyloxycarbonyl-4-aminomethyl-3-pyrrolidone, and the N-tertbutyloxycarbonyl-4-aminomethyl-3-pyrrolidone is transformed into the gemifloxacin side chain 4-aminomethyl-3-methoxyiminopyrrolidone. The preparation method has simple processes, allows mild reaction conditions easily to be realized, has a low raw material price, a low cost and less environmental pollution and creates a novel gemifloxacin side chain pyrrolidone ketonic group protection method and a gemifloxacin side chain synthesis route.

Gemifloxacin intermediate preparation method

The invention relates to medicine and related fields, and especially relates to a gemifloxacin intermediate preparation method. According to the invention, acrylonitrile and ethyl glycinate hydrochloride are adopted as initial raw materials; through the processes of a nucleophilic addition reaction, amino protection, condensation, reduction protection, oxidation, oximation and deprotection, the gemifloxacin branched-chain intermediate 4-aminomethylpyrrolidin-3-one-O-methyloxime dihydrochloride is obtained. The route is simple; two steps of reactions are eliminated; raw materials are cheap and easy to obtain; and product yield is high. The route does not need column chromatography separation. The method provides a feasible synthesis route for industrial production.

Structure-activity-relationship of amide and sulfonamide analogs of omarigliptin

A series of novel substituted-[(3R)-amino-2-(2,5-difluorophenyl)]tetrahydro-2H-pyran analogs have been prepared and evaluated as potent, selective and orally active DPP-4 inhibitors. These efforts lead to the discovery of a long acting DPP-4 inhibitor, omarigliptin (MK-3102), which recently completed phase III clinical development and has been approved in Japan.