Benzyl (2S,5R)-5-[(benzyloxy)amino]piperidine-2-carboxylate ethanedioate
- Product Name
- Benzyl (2S,5R)-5-[(benzyloxy)amino]piperidine-2-carboxylate ethanedioate
- CAS No.
- 1171080-45-7
- Chemical Name
- Benzyl (2S,5R)-5-[(benzyloxy)amino]piperidine-2-carboxylate ethanedioate
- Synonyms
- Avibatan intermediate;Difethialone Impurity 3;Avibactam Intermediate 3;(2S,5R)-5-[(benzyloxy)amino]piperidine-2-carboxylic acid ben...;benzyl(2S,5R)-5-((benzyloxy)amino)piperdine-2-carboxylate oxalate;benzyl(2S,5R)-5-((benzyloxy)amino)piperidine-2-carboxylateoxalate;(2S,5R)-Benzyl 5-((benzyloxy)amino)piperidine-2-carboxylate oxalate;(2S, 5R) -5-[(benzoxy) amino] piperidine-2-benzyl carboxylate, edioate;Benzyl (2S,5R)-5-[(benzyloxy)amino]piperidine-2-carboxylate ethanedioate;(2S,5R)-5-Benzyloxyamino-piperidine-2-carboxylic acid benzyl ester oxalate
- CBNumber
- CB53044363
- Molecular Formula
- C22H26N2O7
- Formula Weight
- 430.46
- MOL File
- 1171080-45-7.mol
Benzyl (2S,5R)-5-[(benzyloxy)amino]piperidine-2-carboxylate ethanedioate Property
- storage temp.
- Inert atmosphere,Room Temperature
- Appearance
- White to off-white Solid
- InChI
- InChI=1/C20H24N2O3.C2H2O4/c23-20(24-14-16-7-3-1-4-8-16)19-12-11-18(13-21-19)22-25-15-17-9-5-2-6-10-17;3-1(4)2(5)6/h1-10,18-19,21-22H,11-15H2;(H,3,4)(H,5,6)/t18-,19+;/s3
- InChIKey
- AMOSSTKBTVKFNW-DSCXOBNPNA-N
- SMILES
- C(=O)(O)C(=O)O.C([C@H]1NC[C@H](NOCC2C=CC=CC=2)CC1)(=O)OCC1C=CC=CC=1 |&1:7,10,r|
Hazard and Precautionary Statements (GHS)
- Symbol(GHS)
-
- Signal word
- Danger
- Hazard statements
-
H225Highly Flammable liquid and vapour
H302Harmful if swallowed
H315Causes skin irritation
H319Causes serious eye irritation
H335May cause respiratory irritation
- Precautionary statements
-
P210Keep away from heat/sparks/open flames/hot surfaces. — No smoking.
P240Ground/bond container and receiving equipment.
P241Use explosion-proof electrical/ventilating/lighting/…/equipment.
P242Use only non-sparking tools.
P243Take precautionary measures against static discharge.
P261Avoid breathing dust/fume/gas/mist/vapours/spray.
P264Wash hands thoroughly after handling.
P264Wash skin thouroughly after handling.
P270Do not eat, drink or smoke when using this product.
P271Use only outdoors or in a well-ventilated area.
P280Wear protective gloves/protective clothing/eye protection/face protection.
P303+P361+P353IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.
P304+P340IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.
P312Call a POISON CENTER or doctor/physician if you feel unwell.
P330Rinse mouth.
P363Wash contaminated clothing before reuse.
P370+P378In case of fire: Use … for extinction.
P403+P233Store in a well-ventilated place. Keep container tightly closed.
P501Dispose of contents/container to..…
N-Bromosuccinimide Price
- Product number
- P482603
- Product name
- (2S,5R)-Benzyl5-((Benzyloxy)amino)piperidine-2-carboxylateOxalate
- Packaging
- 10mg
- Price
- $45
- Updated
- 2021/12/16
- Product number
- CS-M3164
- Product name
- 2-Piperidinecarboxylicacid,5-[(phenylmethoxy)amino]-,phenylmethylester,(2S,5R)-ethanedioate
- Packaging
- 1g
- Price
- $66
- Updated
- 2021/12/16
- Product number
- CS-M3164
- Product name
- 2-Piperidinecarboxylicacid,5-[(phenylmethoxy)amino]-,phenylmethylester,(2S,5R)-ethanedioate
- Packaging
- 5g
- Price
- $202
- Updated
- 2021/12/16
- Product number
- CD11342169
- Product name
- (2S,5R)-Benzyl5-((benzyloxy)amino)piperidine-2-carboxylateoxalate
- Purity
- 97%
- Packaging
- 5g
- Price
- $356
- Updated
- 2021/12/16
- Product number
- 1171080457
- Product name
- (2S,5R)-Benzyl5-((benzyloxy)amino)piperidine-2-carboxylateoxalate
- Packaging
- 5g
- Price
- $400
- Updated
- 2021/12/16
Benzyl (2S,5R)-5-[(benzyloxy)amino]piperidine-2-carboxylate ethanedioate Chemical Properties,Usage,Production
Uses
(2S,5R)-Benzyl 5-((benzyloxy)amino)piperidine-2-carboxylate Oxalate is used as a reactant in the synthesis of Avibactam.
Synthesis
1133931-74-4
144-62-7
1171080-45-7
In a 2000-mL four-neck flask, 500 g of ethyl acetate and 135.0 g (0.4 mol) of benzyl (S,E)-5-((benzyloxy)imino)piperidine-2-carboxylate (III3) were added, a thermometer was mounted and the reaction temperature was maintained at between -20°C and -15°C. 201.0 g of concentrated sulfuric acid (2.0 moles) was slowly added dropwise, and stirring was continued for 1 hour after the drop was completed. At -20°C, 190.0 g (0.9 mol) of sodium triacetoxyborohydride was added in batches and the reaction was stirred for 5 hours keeping the reaction temperature between -20°C and -15°C. Upon completion of the reaction, keeping the temperature below 0 °C, 200 g of water was slowly added to quench the reaction, followed by neutralization with ammonia to a system pH of 7-8. The organic and aqueous layers were separated and the organic layer was washed twice with deionized water. The organic phase was concentrated under reduced pressure to recover the solvent. To the residue was added 320 g of ethyl acetate and 160 g of methanol, followed by 52.0 g (0.42 mol) of oxalic acid dihydrate, heated to 45 °C and stirred for 2 hours. The reaction solution was cooled to room temperature and filtered, and the filter cake was washed with 100 g of a solvent mixture of ethyl acetate/methanol (2:1, v/v), and then with 50 g of ethyl acetate. All filtrates were combined and reserved for subsequent steps. The filter cake was dried under vacuum to afford 118.8 g of (2S,5R)-benzyl 5-((benzyloxy)amino)piperidine-2-carboxylic acid ethyl ester oxalate, with 99.7% purity and 69.0% 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 14-15
Benzyl (2S,5R)-5-[(benzyloxy)amino]piperidine-2-carboxylate ethanedioate Preparation Products And Raw materials
Raw materials
Preparation Products
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View Lastest Price from Benzyl (2S,5R)-5-[(benzyloxy)amino]piperidine-2-carboxylate ethanedioate manufacturers
- Product
- Benzyl (2S,5R)-5-[(benzyloxy)amino]piperidine-2-carboxylate ethanedioate 1171080-45-7
- Price
- US $100.00/KG
- Min. Order
- 100G
- Purity
- 98%
- Supply Ability
- 10KG,25KG
- Release date
- 2018-07-25