Boc-3-amino-2,2-dimethyl-propionic acid Chemical Properties

Boiling point:

346.5±25.0 °C(Predicted)

Density 

1.082±0.06 g/cm3(Predicted)

storage temp. 

Sealed in dry,Room Temperature

form 

powder

pka

4.61±0.10(Predicted)

Appearance

White to off-white Solid

Safety Information

HS Code 

29225090

Boc-3-amino-2,2-dimethyl-propionic acid Usage And Synthesis

Uses

2,2-Dimethyl-β-alanine-N-(tert-butoxycarbonyl) is used as a reactant in the synthesis of cryptophycin anticancer agents.

Synthesis

Example 6: Synthesis of 3-(tert-butoxycarbonylamino)-2,2-dimethylpropionic acid (19) [00156] Under argon protection, 3-amino-2,2-dimethylpropionic acid (18) (1.2 g, 10.2 mmol), di-tert-butyl dicarbonate (Boc anhydride) (2.3 g, 10.2 mmol) and N,N-diisopropylethylamine (DIPEA) (1.85 mL, 10.23 mmol) were dissolved in N,N-dimethylformamide (DMF) (30 mL) in N,N-dimethylformamide (DMF) and the reaction was stirred at 60°C for 16 hours. After completion of the reaction, the reaction mixture was concentrated under reduced pressure, the residue was dissolved in ethyl acetate (EtOAc), washed with saturated ammonium chloride (NH4Cl) solution, and the organic phase was concentrated again under reduced pressure to afford the title compound 3-(tert-butoxycarbonylamino)-2,2-dimethylpropanoic acid (19) (2.0 g, 91% yield). 1H NMR (300 MHz, CDCl3) δ 1.33 (s, 6H), 1.37 (s, 9H), 2.69 (s, 2H).

References

[1] Patent: WO2011/32291, 2011, A1. Location in patent: Page/Page column 47
[2] Journal of Organic Chemistry, 2010, vol. 75, # 20, p. 6953 - 6960
[3] Patent: US2015/210635, 2015, A1. Location in patent: Paragraph 0483-0485
[4] Patent: EP2865664, 2015, A1. Location in patent: Paragraph 0105; 0106
[5] Tetrahedron Letters, 2007, vol. 48, # 47, p. 8277 - 8280

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