| Identification | Back Directory | [Name]
Avibactam INT 1 | [CAS]
1416134-48-9 | [Synonyms]
Avibactam INT
Avibactam IM-1
Avibactam INT 1
Avibactam-002-oxalate
Avibactam Impurity 51
Avibactam Intermediate
Avibactam Intermediate 1
Avivabine sodium intermediate 1
ethyl (2S,5R)-5-[(benzyloxy)amino]piperidine-2-carboxylate
ethyl(2S,5R)-5-((benzyloxy)amino)piperdine-2-carboxylate oxalate
(2S, 5R) -benzyloxyaminopiperidine-2-carboxylic acid ethyl oxalate
ethyl (2S,5R)-5-((benzyloxy)amino)piperidine-2-carboxylate oxalate
(2S,5R)-5-[(Benzyloxy)amino]piperidine-2-carboxylate ethyl oxalate
(2S,5R)-Methyl-5-[(benzyloxy)amino]piperidine-2-carboxylate ethanedioate
(2S,5R)-5-Methyl-5-[(benzyloxy)amino]piperidine-2-carboxylate ethanedioate
(2S,5R)-Methyl-5-[(benzyloxy)amino]piperidine-2-carboxylate ethanedioate (1:1)
(2S,5R)-5-[(Phenylmethoxy)amino]-2-piperidinecarboxylic acid ethyl ester ethanedioate
(2S,5R)-5-[(benzyloxy)amino]piperidine-2-carboxylic acid ethyl ester ethanedioate
2-Piperidinecarboxylic acid, 5-[(phenylmethoxy)amino]-, ethyl ester, (2S,5R)-, ethanedioate (1:1) | [Molecular Formula]
C15H22N2O3.C2H2O4 | [MDL Number]
MFCD29918783 | [MOL File]
1416134-48-9.mol | [Molecular Weight]
368.382 |
| Questions And Answer | Back Directory | [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. |
| Chemical Properties | Back Directory | [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| |
| Hazard Information | Back Directory | [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]
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 |
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