Identification | Back Directory | [Name]
Boc-3-amino-2,2-dimethyl-propionic acid | [CAS]
180181-02-6 | [Synonyms]
N-Boc-3-Amino-2,2-dimethyl-propi 3-BOCAMINO-2,2-DIMETHYL-PROPIONIC ACID Boc-3-amino-2,2-dimethyl-propionic acid N-Boc-3-amino-2,2-dimethylpropionic acid 3-(Boc-amino)-2,2-dimethylpropanoic acid 2,2-Dimethyl-β-alanine-N-(tert-butoxycarbonyl) 3-(tert-butoxycarbonyl)-2,2-dimethylpropanoic acid tert-butyl 3-allyl-3-hydroxyazetidine-41-carboxylate 3-((tert-Butoxycarbonyl)aMino)-2,2-diMethylpropanoic acid 2,2-Dimethyl-3-[(2-methylpropan-2-yl)oxycarbonylamino]propanoic acid Propanoic acid, 3-[[(1,1-dimethylethoxy)carbonyl]amino]-2,2-dimethyl- | [Molecular Formula]
C10H19NO4 | [MDL Number]
MFCD09952625 | [MOL File]
180181-02-6.mol | [Molecular Weight]
217.26 |
Chemical Properties | Back Directory | [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 |
Hazard Information | Back Directory | [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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