tert-butyl 3-aminopropanoate Chemical Properties

Boiling point:

192 ºC

Density 

0.959

Flash point:

64 ºC

storage temp. 

Keep in dark place,Inert atmosphere,Store in freezer, under -20°C

pka

8.67±0.10(Predicted)

form 

liquid

color 

Colourless

Safety Information

HS Code 

2922498590

tert-butyl 3-aminopropanoate Usage And Synthesis

Uses

tert-Butyl 3-Aminopropanoate is an intermediate useful in the synthesis of rac-3-Oxo Atorvastatin Sodium Salt (O847150), which is a byproduct impurity of Atorvastatin Calcium (A791750), a selective, competitive HMG-CoA reductase inhibitor. Atorvastatin is the only drug in its class specfically indicated for lowering both elevated LDL-cholesterol and triglyceinhibitorrides in patients with hypercholesterolemia.

Synthesis

The general procedure for the synthesis of tert-butyl 3-aminopropionate from tert-butyl cyanoacetate is as follows: 200 g of tert-butyl cyanoacetate was added to the reactor, followed by the addition of 1 kg of 2% methanol-ammonia aqueous solution and 20 g of Ruannei nickel. The reaction kettle was sealed and replaced three times with nitrogen and then three times with hydrogen. The hydrogen pressure was adjusted to 5 MPa, heated to 55 °C, and the reaction was carried out under stirring for 6 h, during which the hydrogen was continuously replenished. Upon completion of the reaction, the catalyst was removed by filtration and the filtrate was concentrated to about 200 g and diluted with ethyl acetate. After cooling, the pH was adjusted to 3 with ethyl acetate-hydrogen chloride solution, the reaction system was concentrated again and the precipitated solid was dried to give 198 g of the target product tert-butyl 3-aminopropionate.

IC 50

Alkyl/ether

References

[1] Patent: CN105367435, 2016, A. Location in patent: Paragraph 0022; 0023

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