Avibactam INT 1
Uses- Product Name
- Avibactam INT 1
- CAS No.
- 1416134-48-9
- Chemical Name
- Avibactam INT 1
- Synonyms
- ethyl (2S,5R)-5-((benzyloxy)amino)piperidine-2-carboxylate oxalate;(2S,5R)-Methyl-5-[(benzyloxy)amino]piperidine-2-carboxylate ethanedioate;Avibactam INT;Avibactam IM-1;Avibactam INT 1;Avibactam-002-oxalate;Avibactam Impurity 51;Ethyl formate oxalate;Avibactam Intermediate;Avibactam Intermediate 1
- CBNumber
- CB12747096
- Molecular Formula
- C17H24N2O7
- Formula Weight
- 368.39
- MOL File
- 1416134-48-9.mol
Avibactam INT 1 Property
- storage temp.
- Inert atmosphere,Room Temperature
- form
- Solid
- color
- White to Yellow
- InChI
- InChI=1/C15H22N2O3.C2H2O4/c1-2-19-15(18)14-9-8-13(10-16-14)17-20-11-12-6-4-3-5-7-12;3-1(4)2(5)6/h3-7,13-14,16-17H,2,8-11H2,1H3;(H,3,4)(H,5,6)/t13-,14+;/s3
- InChIKey
- PYUXATUBICTSNB-PWTHNFALNA-N
- SMILES
- C(=O)(O)C(=O)O.N([C@H]1CN[C@H](C(=O)OCC)CC1)OCC1C=CC=CC=1 |&1:7,10,r|
N-Bromosuccinimide Price
- Product number
- P335570
- Product name
- (2S,5R)-5-[(Phenylmethoxy)amino]-2-piperidinecarboxylicAcidEthylEsterEthanedioate
- Packaging
- 5mg
- Price
- $345
- Updated
- 2021/12/16
- Product number
- CS-M3476
- Product name
- (2S,5R)-Ethyl5-((benzyloxy)amino)piperidine-2-carboxylateoxalate
- Purity
- 99.75%
- Packaging
- 10g
- Price
- $50
- Updated
- 2021/12/16
- Product number
- CS-M3476
- Product name
- (2S,5R)-Ethyl5-((benzyloxy)amino)piperidine-2-carboxylateoxalate
- Purity
- 99.75%
- Packaging
- 25g
- Price
- $90
- Updated
- 2021/12/16
- Product number
- 6348EA
- Product name
- (2S,5R)-Ethyl5-((benzyloxy)amino)piperidine-2-carboxylateoxalate
- Packaging
- 10g
- Price
- $166
- Updated
- 2021/12/16
- Product number
- CS-M3476
- Product name
- (2S,5R)-Ethyl5-((benzyloxy)amino)piperidine-2-carboxylateoxalate
- Purity
- 99.75%
- Packaging
- 100g
- Price
- $300
- Updated
- 2021/12/16
Avibactam INT 1 Chemical Properties,Usage,Production
Uses
(2S,5R)-5-[(Phenylmethoxy)amino]-2-piperidinecarboxylic Acid Ethyl Ester Ethanedioate is an impurity of Avibactam; a novel β-lactamase inhibitor with a non-lactam structural scaffold. Avibactam irreversibly inhibits lactamase from Mycobacterium tuberculosis.
Description
Avibactam INT 1, chemically known as (2S,5R)-Ethyl 5-((benzyloxy)amino)piperidine-2-carboxylate oxalate, is an Avibactam impurity. It is used as an impurity control reagent and also for drug declaration testing, etc.
Synthesis
1416134-60-5
144-62-7
1416134-48-9
In a 2000 mL four-necked flask fitted with a stirring device and a thermometer inserted, 500 g of ethyl acetate and 110.0 g (0.4 mol) of ethyl 5-benzyloxyiminopiperidine-2-carboxylate (III2) were added. The reaction system was cooled to -20 °C to -15 °C and 201.0 g (2.0 mol) of concentrated sulfuric acid was slowly added dropwise. After the dropwise addition was completed, the reaction continued to be stirred at -20 °C for 1 hour. Subsequently, 190.0 g (0.9 mol) of sodium triacetoxyborohydride was added in batches at -20 °C, and the reaction was stirred for 5 hours keeping the temperature in the range of -20 °C to -15 °C. Upon completion of the reaction, the temperature was controlled below 0 °C and the reaction was quenched by slow addition of 200 g of water and neutralized with ammonia to pH 7-8. The organic layer was separated and washed twice with 100 g of saturated brine. The organic phase was concentrated to recover the solvent and 320 g of ethyl acetate and 160 g of methanol were added to the residue, followed by 52.0 g (0.42 mol) of oxalic acid dihydrate. The mixture was heated to 45°C, stirred for 2 hours and then cooled to room temperature and filtered. The filter cake was washed with 100 g ethyl acetate/methanol (2:1) solvent mixture and then with 50 g ethyl acetate. All filtrates were combined for use in subsequent steps. The filter cake was dried under vacuum to give 96.3 g of the single isomer (2S,5R)-5-((benzyloxy)amino)piperidine-2-carboxylic acid ethyl ester oxalate, with 99.6% purity and 65.4% yield by chiral HPLC.
References
[1] Patent: CN107540600, 2018, A. Location in patent: Paragraph 0052-0054
[2] Patent: US2012/323010, 2012, A1. Location in patent: Page/Page column 17-18
Avibactam INT 1 Preparation Products And Raw materials
Raw materials
Preparation Products
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View Lastest Price from Avibactam INT 1 manufacturers
- Product
- Avibactam INT 1 1416134-48-9
- Price
- US $0.00-0.00/kg
- Min. Order
- 1kg
- Purity
- 98%
- Supply Ability
- 1Ton
- Release date
- 2022-09-29
- Product
- Avibactam INT 1 1416134-48-9
- Price
- US $1.00/kg
- Min. Order
- 1kg
- Purity
- 99
- Supply Ability
- 200
- Release date
- 2024-08-01
- Product
- Avibactam INT 1 1416134-48-9
- Price
- US $0.00/kg
- Min. Order
- 1kg
- Purity
- 99%
- Supply Ability
- 10000KGS
- Release date
- 2025-03-05