1-N-Cbz-belta-Proline Chemical Properties

Boiling point:

432.3±45.0 °C(Predicted)

Density 

1.309±0.06 g/cm3(Predicted)

storage temp. 

under inert gas (nitrogen or Argon) at 2-8°C

pka

4.46±0.20(Predicted)

form 

Solid

Appearance

White to off-white Solid

CAS DataBase Reference

188527-21-1(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

43

Safety Statements 

36/37

1-N-Cbz-belta-Proline Usage And Synthesis

Uses

1-?(Benzyloxycarbonyl)?pyrrolidine-?3-?carboxylic Acid is a reagent used in the synthesis of cyclin-dependent kinase 4-inhibitors (CDK4) for cancer treatments. Also used towards the discovery of a potent inhibitor of poly(ADP-ribose) polymerase (PARP) for the treatment of cancer pased upon benzimidazole carboxamide moieties.

Synthesis

To a 250 mL multi-necked round-bottomed flask was added 8.1 g (30.8 mmol) of 1-benzyl 3-methylpyrrolidine-1,3-dicarboxylate and 80 mL of tetrahydrofuran, and 80 mL of an aqueous solution of lithium hydroxide of 3.9 g (92.4 mmol) was added slowly dropwise.The reaction mixture was stirred for 1 hr at 0 °C, followed by stirring at room temperature overnight. Upon completion of the reaction, the mixture was washed with ether and the pH of the mixture was adjusted to 5-6 with 0.5 M hydrochloric acid. the mixture was extracted three times with 30 mL of ethyl acetate, and the organic phases were combined. The organic phase was dried with anhydrous sodium sulfate, filtered, and the filtrate was concentrated under reduced pressure to give 7.3 g of 1-Cbz-3-pyrrolidinecarboxylic acid as a yellow oil in 95% yield.

References

[1] Patent: CN104817549, 2017, B. Location in patent: Paragraph 0044-0046

1-N-Cbz-belta-Proline(188527-21-1)Related Product Information

• 1-N-CBZ-PYRROLIDINE-3-CARBOXYLIC ACID
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• 1-CBZ-PYRROLIDINE-3-CARBOXYLIC ACID ETHYL ESTER
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• 4-PHENYL-PYRROLIDINE-1,3-DICARBOXYLIC ACID 1-BENZYL ESTER
• 4-(4-METHOXY-PHENYL)-PYRROLIDINE-1,3-DICARBOXYLIC ACID 1-BENZYL ESTER
• 4-(2-CHLORO-PHENYL)-PYRROLIDINE-1,3-DICARBOXYLIC ACID 1-BENZYL ESTER
• 4-(4-CHLORO-PHENYL)-PYRROLIDINE-1,3-DICARBOXYLIC ACID 1-BENZYL ESTER