1-{[(1,1-diMethylethyl)oxy]carbonyl}-3-hydroxyazetidine-3-carboxylic acid
- Product Name
- 1-{[(1,1-diMethylethyl)oxy]carbonyl}-3-hydroxyazetidine-3-carboxylic acid
- CAS No.
- 1035351-06-4
- Chemical Name
- 1-{[(1,1-diMethylethyl)oxy]carbonyl}-3-hydroxyazetidine-3-carboxylic acid
- Synonyms
- 1-Boc-3-hydroxyazetidine-3-carboxylic Acid;1-[(tert-butoxy)carbonyl]-3-hydroxyazetidine-3-carboxylic acid;3-Hydroxy-azetidine-1,3-dicarboxylic acid mono-tert-butyl ester;1,3-Azetidinedicarboxylic acid, 3-hydroxy-, 1-(1,1-dimethylethyl) ester;1-{[(1,1-diMethylethyl)oxy]carbonyl}-3-hydroxyazetidine-3-carboxylic acid;3-hydroxy-1-[(2-methylpropan-2-yl)oxycarbonyl]azetidine-3-carboxylic Acid
- CBNumber
- CB02655206
- Molecular Formula
- C9H15NO5
- Formula Weight
- 217.22
- MOL File
- 1035351-06-4.mol
1-{[(1,1-diMethylethyl)oxy]carbonyl}-3-hydroxyazetidine-3-carboxylic acid Property
- Boiling point:
- 371.3±42.0 °C(Predicted)
- Density
- 1.384±0.06 g/cm3(Predicted)
- storage temp.
- 2-8°C
- pka
- 3.57±0.20(Predicted)
- Appearance
- White to off-white Solid
Hazard and Precautionary Statements (GHS)
- Symbol(GHS)
-
- Signal word
- Warning
- Hazard statements
-
H302Harmful if swallowed
H315Causes skin irritation
H319Causes serious eye irritation
H335May cause respiratory irritation
- Precautionary statements
-
P261Avoid breathing dust/fume/gas/mist/vapours/spray.
P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.
N-Bromosuccinimide Price
- Product number
- B702290
- Product name
- 1-[(tert-Butoxy)carbonyl]-3-hydroxyazetidine-3-carboxylicAcid
- Packaging
- 10mg
- Price
- $45
- Updated
- 2021/12/16
- Product number
- B702290
- Product name
- 1-[(tert-Butoxy)carbonyl]-3-hydroxyazetidine-3-carboxylicAcid
- Packaging
- 100mg
- Price
- $240
- Updated
- 2021/12/16
- Product number
- CHM1051960
- Product name
- 1-[(TERT-BUTOXY)CARBONYL]-3-HYDROXYAZETIDINE-3-CARBOXYLIC ACID
- Purity
- 95.00%
- Packaging
- 5MG
- Price
- $452.74
- Updated
- 2021/12/16
- Product number
- 6669DP
- Product name
- 1-(Tert-Butoxycarbonyl)-3-hydroxyazetidine-3-carboxylicacid
- Packaging
- 10g
- Price
- $2598
- Updated
- 2021/12/16
- Product number
- CM200417
- Product name
- 1-(tert-Butoxycarbonyl)-3-hydroxyazetidine-3-carboxylicacid
- Purity
- 95%
- Packaging
- 1g
- Price
- $771
- Updated
- 2021/12/16
1-{[(1,1-diMethylethyl)oxy]carbonyl}-3-hydroxyazetidine-3-carboxylic acid Chemical Properties,Usage,Production
Synthesis
398489-26-4
7677-24-9
24424-99-5
1035351-06-4
Under argon protection, tert-butyl 3-oxoazetidine-1-carboxylate (2.0 g, 11.7 mmol) was dissolved in THF (50 mL), a catalytic amount of ZnI2 (0.11 mg) was added followed by the dropwise addition of trimethylcyanosilane (TMSCN, 1.62 g, 16.4 mmol). The reaction mixture was stirred at room temperature for 18 h and then concentrated under reduced pressure to remove the solvent. The residue was dissolved in EtOAc (100 mL), washed sequentially with saturated aqueous NaHCO3 and deionized water, and the organic phase was dried over anhydrous Na2SO4 and concentrated. The obtained residue was dissolved in acetic acid (HOAc, 25 mL), concentrated aqueous hydrochloric acid (25 mL) was added, and the mixture was heated at reflux for 3 hours and concentrated. The residue was dissolved in isopropanol (iPrOH, 20 mL) and 2M NaOH aqueous solution (20 mL) and di-tert-butyl dicarbonate (Boc2O, 1.66 g, 8.0 mmol) was added. After completion of the reaction, iPrOH was removed by rotary evaporation, water (30 mL) was added and extracted with ether (Et2O, 2 × 30 mL). The aqueous phase was acidified with 1N HCl aqueous solution to pH=2 and extracted with EtOAc (3×30 mL). The organic phases were combined, dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure. The crude product was purified by silica gel column chromatography (elution gradient: 100% EtOAc to 1:1 EtOAc:MeOH) to afford 1-(tert-butoxycarbonyl)-3-hydroxyazetidine-3-carboxylic acid (0.17 g, 0.79 mmol, 7% yield).ESMS analysis showed that the target compound, C9H15NO5, had a m/z of 216 (M-H)-.
References
[1] Patent: WO2011/143497, 2011, A1. Location in patent: Page/Page column 49; 50
1-{[(1,1-diMethylethyl)oxy]carbonyl}-3-hydroxyazetidine-3-carboxylic acid Preparation Products And Raw materials
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