(2-Amino-benzyl)-carbamic acid tert-butyl ester Chemical Properties

Melting point:

93℃

Boiling point:

382.5±25.0 °C(Predicted)

Density 

1.095±0.06 g/cm3 (20 ºC 760 Torr)

storage temp. 

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

pka

12.10±0.46(Predicted)

Appearance

White to off-white Solid

(2-Amino-benzyl)-carbamic acid tert-butyl ester Usage And Synthesis

Synthesis

General procedure for the synthesis of tert-butyl (2-aminobenzyl)-carbamate from di-tert-butyl dicarbonate and 2-aminobenzylamine: 2-aminobenzylamine (6.0 g, 49.2 mmol) was dissolved in dichloromethane and stirred in an ice bath under nitrogen protection. A dichloromethane solution of di-tert-butyl dicarbonate (Boc)2O (10.7 g, 49.2 mmol) was added slowly and dropwise. The reaction mixture was then warmed up to room temperature to continue the reaction. After completion of the reaction, the reaction solution was washed sequentially with distilled water and saturated saline, dried over anhydrous sodium sulfate and filtered. The solvent was removed by distillation under reduced pressure and stirred overnight. The intermediate (2-aminobenzyl)-carbamic acid tert-butyl ester 5,10.5 g was obtained in 96.2% yield.

References

[1] Patent: CN104016944, 2016, B. Location in patent: Paragraph 0014-0015; 0046-0047
[2] Angewandte Chemie - International Edition, 2017, vol. 56, # 7, p. 1885 - 1889
[3] Angew. Chem., 2017, vol. 129, # 7, p. 1911 - 1915,5
[4] Organic and Biomolecular Chemistry, 2011, vol. 9, # 3, p. 656 - 658
[5] Journal of Medicinal Chemistry, 2003, vol. 46, # 9, p. 1661 - 1669

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