1-(BENZYLOXYCARBONYL) AZETIDINE-3-CARBOXYLIC ACID
- Product Name
- 1-(BENZYLOXYCARBONYL) AZETIDINE-3-CARBOXYLIC ACID
- CAS No.
- 97628-92-7
- Chemical Name
- 1-(BENZYLOXYCARBONYL) AZETIDINE-3-CARBOXYLIC ACID
- Synonyms
- 1-Cbz-azetidine-3-carboxy...;Cbz-3-Azetidinecarboxylic acid;CBZ-AZETIDINE-3-CARBOXYLIC ACID;N-Cbz-azetidine-3-carboxylic acid;1-Cbz-azetidine-3-carboxylic acid;N-Carbobenzyloxyazetidine-3-carboxylic acid;1-Cbz-azetidine-3-carboxylic acid - [C1527];Azetidine-1,3-dicarboxylic acid 1-benzyl ester;1-benzyloxycarbonyl-3-azetidinecarboxylic acid;1-(BENZYLOXYCARBONYL) AZETIDINE-3-CARBOXYLIC ACID
- CBNumber
- CB8844563
- Molecular Formula
- C12H13NO4
- Formula Weight
- 235.24
- MOL File
- 97628-92-7.mol
1-(BENZYLOXYCARBONYL) AZETIDINE-3-CARBOXYLIC ACID Property
- Boiling point:
- 421.2±45.0 °C(Predicted)
- Density
- 1.362
- storage temp.
- 2-8°C
- pka
- 4.19±0.20(Predicted)
- form
- Solid
- color
- White to off-white
Safety
- HazardClass
- IRRITANT
- HS Code
- 2933998090
Hazard and Precautionary Statements (GHS)
- Symbol(GHS)
-
- Signal word
- Warning
- Hazard statements
-
H315Causes skin irritation
H319Causes serious eye irritation
H335May cause respiratory irritation
- Precautionary statements
-
P261Avoid breathing dust/fume/gas/mist/vapours/spray.
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.
P405Store locked up.
N-Bromosuccinimide Price
- Product number
- B194110
- Product name
- 1-(Benzyloxycarbonyl)Azetidine-3-carboxylicAcid
- Packaging
- 500mg
- Price
- $45
- Updated
- 2021/12/16
- Product number
- AS3824
- Product name
- 1-(Benzyloxycarbonyl)azetidine-3-carboxylicacid
- Purity
- 95+%
- Packaging
- 1g
- Price
- $32
- Updated
- 2021/12/16
- Product number
- 059922
- Product name
- N-Cbz-Azetidine-3-carboxylic acid
- Purity
- 95%
- Packaging
- 500mg
- Price
- $93
- Updated
- 2021/12/16
- Product number
- 4H58-1-8M
- Product name
- 1-Cbz-azetidine-3-carboxylic acid
- Packaging
- 1g
- Price
- $120
- Updated
- 2021/12/16
- Product number
- FB139889
- Product name
- 1-((Benzyloxy)carbonyl)azetidine-3-carboxylic acid
- Packaging
- 5G
- Price
- $126
- Updated
- 2021/12/16
1-(BENZYLOXYCARBONYL) AZETIDINE-3-CARBOXYLIC ACID Chemical Properties,Usage,Production
Uses
1-Cbz-azetidine-3-carboxylic acid is a non-cleavable ADC linker used in the synthesis of antibody-drug conjugates (ADCs). 1-Cbz-azetidine-3-carboxylic acid is also a alkyl chain-based PROTAC linker that can be used in the synthesis of PROTACs[1]
Synthesis
36476-78-5
501-53-1
97628-92-7
General procedure for the synthesis of 1-(benzyloxycarbonyl)azetidine-3-carboxylic acid from 3-acridinecarboxylic acid and benzyl chloroformate: 3-acridinecarboxylic acid (4.0 g, 39.6 mmol) was dissolved in a 1 N sodium hydroxide solution (40 mL) and the solution was cooled to 0 °C. Under stirring, benzyl chloroformate (5.9 mL, 41 mmol) was slowly added, followed by dropwise addition of additional 1 N sodium hydroxide solution (41 mL). The reaction mixture was stirred vigorously at 0 °C for 16 hours. Upon completion of the reaction, the mixture was acidified to a pH of about 2-3 with 2 N hydrochloric acid.The acidified suspension was extracted with dichloromethane (2 x 100 mL) and the organic layers were combined and dried with anhydrous magnesium sulfate. After filtration, the organic phase was concentrated under reduced pressure to afford the white solid product 1-(benzyloxycarbonyl)azetidine-3-carboxylic acid (9.3 g, 39.6 mmol, 100% yield). The structure of the product was confirmed by 1H NMR (400 MHz, CDCl3): δ 7.37-7.29 (5H, m, Ar-H), 5.10 (2H, s, CH2Ph), 4.21 (4H, d, J = 7.5 Hz, NCH2), 3.43 (1H, quintuple peak, J = 7.5 Hz, CH).
IC 50
Non-cleavable Linker
References
[1] Beck A, et al. Strategies and challenges for the next generation of antibody-drug conjugates. Nat Rev Drug Discov. 2017;16(5):315-337. DOI:10.1038/nrd.2016.268
[2] Nalawansha DA, et al. PROTACs: An Emerging Therapeutic Modality in Precision Medicine. Cell Chem Biol. 2020;27(8):998-985. DOI:10.7554/eLife.57277
1-(BENZYLOXYCARBONYL) AZETIDINE-3-CARBOXYLIC ACID Preparation Products And Raw materials
Raw materials
Preparation Products
1-(BENZYLOXYCARBONYL) AZETIDINE-3-CARBOXYLIC ACID Suppliers
- Tel
- +86-21-20908456
- Fax
- 021-58180499
- sales@BioChemBest.com
- Country
- China
- ProdList
- 6003
- Advantage
- 61
- Tel
- 400-6106006
- Fax
- 021-67582001/03/05
- saleschina@alfa-asia.com
- Country
- China
- ProdList
- 30123
- Advantage
- 84
- Tel
- 021-021-58432009 400-005-6266
- Fax
- 021-58436166
- sales8178@energy-chemical.com
- Country
- China
- ProdList
- 44802
- Advantage
- 61
- Tel
- 13817811078
- Fax
- 86-021-50426522,50426273
- sales@jingyan-chemical.com
- Country
- China
- ProdList
- 9976
- Advantage
- 60
- Tel
- 021-50795510 4000665055
- Fax
- 021-50795055
- sales@accelachem.com
- Country
- China
- ProdList
- 11032
- Advantage
- 64
- Tel
- 021-34975603-808 18721111801
- Fax
- +86-21-34975602-805
- sales@bocpharma.com
- Country
- China
- ProdList
- 1003
- Advantage
- 64
- Tel
- 021-54306202 13764082696
- info@hanhongsci.com
- Country
- China
- ProdList
- 42934
- Advantage
- 64
- Tel
- 18270980682
- Fax
- 021 51613951
- mlcheng@sunwaypharm.cn
- Country
- China
- ProdList
- 8667
- Advantage
- 57
- Tel
- +86-028-82550498 +86-19102685862
- Fax
- 086-28-82550468
- sales@pu-kang.com
- Country
- China
- ProdList
- 497
- Advantage
- 58
- Tel
- +86-21-60341587
- Fax
- +86-21-61294319
- sales@topbiochem.com
- Country
- China
- ProdList
- 6175
- Advantage
- 58