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HomeProduct name listAzetidine-1,2-dicarboxylic acid 1-tert-butyl ester

Azetidine-1,2-dicarboxylic acid 1-tert-butyl ester

Azetidine-1,2-dicarboxylic acid 1-tert-butyl ester Structural

What is Azetidine-1,2-dicarboxylic acid 1-tert-butyl ester?

Description

Azetidine-1,2-dicarboxylic acid 1-tert-butyl ester (ADCBT) is a pyrrolidinyl nicotinic acetylcholine receptor agonist. ADCBT has been shown to have affinity values for neuronal nicotinic acetylcholine receptors that are significantly higher than those of nicotine. It has been shown to be regioselective in the sense that it binds preferentially to the alpha4beta2 subtype of the nicotinic acetylcholine receptor, which is present in both peripheral and central neurons. It also has a high affinity for the acetylcholine binding site at the neuromuscular junction. ADCBT has been shown to have analgesic effects in animal studies.

Chemical properties

White powder

The Uses of Azetidine-1,2-dicarboxylic acid 1-tert-butyl ester

1,2-Azetidinedicarboxylic Acid 1-(1,1-Dimethylethyl) Ester, is an useful intermediate in the synthesis of pharmaceutical compounds including inhibitors and receptor Antagonists. It can be used in the synthesis of polypeptides.

Preparation

Sodium hydroxide (2.08 g, 51.92 mmol) was added to a solution of azetidine-2-carboxylic acid (5.00 g, 49.50 mmol), di-tert-butyl dicarbonate (13.50 g, 61.80 mmol) in ethanol (120.0 mL) at 0 °C. After stirring the reaction mixture for 8 hours, the pH of the mixture was adjusted to 2 with 1.0 N HCl and extracted with ethyl acetate (2 × 200 mL). The combined organic layers were washed with brine, separated, and dried over anhydrous sodium sulfate. Then the compound was concentrated under reduced pressure to afford Azetidine-1,2-dicarboxylic acid 1-tert-butyl ester.
AZETIDINE-1,2-DICARBOXYLIC ACID 1-TERT-BUTYL ESTER

Properties of Azetidine-1,2-dicarboxylic acid 1-tert-butyl ester

Boiling point: 321.0±35.0 °C(Predicted)
Density  1.246±0.06 g/cm3(Predicted)
storage temp.  2-8°C
pka 4.01±0.20(Predicted)
color  Pale yellow

Safety information for Azetidine-1,2-dicarboxylic acid 1-tert-butyl ester

Signal word Warning
Pictogram(s)
ghs
Exclamation Mark
Irritant
GHS07
GHS Hazard Statements H302:Acute toxicity,oral
H315:Skin corrosion/irritation
H319:Serious eye damage/eye irritation
H335:Specific target organ toxicity, single exposure;Respiratory tract irritation
Precautionary Statement Codes P261:Avoid breathing dust/fume/gas/mist/vapours/spray.
P305+P351+P338:IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

Computed Descriptors for Azetidine-1,2-dicarboxylic acid 1-tert-butyl ester

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