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

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)

form 

solid

color 

Pale yellow

Safety Information

Hazard Codes 

Xi,N

Risk Statements 

36/37/38-50

Safety Statements 

26-36-61-24/25

RIDADR 

UN3077

WGK Germany 

3

HS Code 

29339900

MSDS

• Language:English Provider:SigmaAldrich

Azetidine-1,2-dicarboxylic acid 1-tert-butyl ester Usage And Synthesis

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

Uses

Azetidine-1,2-dicarboxylic acid 1-tert-butyl 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(159749-28-7)Related Product Information

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• (S)-Azetidine-1,2-dicarboxylic acid 1-tert-butyl ester
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• AZETIDINE-1,2-DICARBOXYLIC ACID 1-TERT-BUTYL ESTER 2-METHYL ESTER
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• AZETIDINE-1,3-DICARBOXYLIC ACID MONO-TERT-BUTYL ESTER
• (S)-N-BOC-AZETIDINE-2-CARBOXYLIC ACID METHYL ESTER
• AZETIDINE-1,2-DICARBOXYLIC ACID 1-TERT-BUTYL ESTER 2-ETHYL ESTER
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• Azetidine-1,2-dicarboxylic acid 1-tert-butyl ester