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

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Boc-3-amino-2,2-dimethyl-propionic acid Basic information
Product Name:Boc-3-amino-2,2-dimethyl-propionic acid
Synonyms:Boc-3-amino-2,2-dimethyl-propionic acid;3-(tert-butoxycarbonyl)-2,2-dimethylpropanoic acid;Propanoic acid, 3-[[(1,1-dimethylethoxy)carbonyl]amino]-2,2-dimethyl-;2,2-Dimethyl-3-[(2-methylpropan-2-yl)oxycarbonylamino]propanoic acid;N-Boc-3-amino-2,2-dimethylpropionic acid;3-((tert-Butoxycarbonyl)aMino)-2,2-diMethylpropanoic acid;3-BOCAMINO-2,2-DIMETHYL-PROPIONIC ACID;3-(Boc-amino)-2,2-dimethylpropanoic acid
CAS:180181-02-6
MF:C10H19NO4
MW:217.26
EINECS:
Product Categories:
Mol File:180181-02-6.mol
Boc-3-amino-2,2-dimethyl-propionic acid Structure
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
pka4.61±0.10(Predicted)
AppearanceWhite to off-white Solid
InChI1S/C10H18O4/c1-9(2,3)14-7(11)6-10(4,5)8(12)13/h6H2,1-5H3,(H,12,13)
InChIKeyBCUIGUVXRMEZDV-UHFFFAOYSA-N
SMILESCC(C)(C)OC(CC(C)(C(O)=O)C)=O
Safety Information
WGK Germany WGK 3
HS Code 29225090
Storage Class11 - Combustible Solids
Hazard ClassificationsAcute Tox. 4 Oral
MSDS Information
Boc-3-amino-2,2-dimethyl-propionic acid Usage And Synthesis
Uses2,2-Dimethyl-β-alanine-N-(tert-butoxycarbonyl) is used as a reactant in the synthesis of cryptophycin anticancer agents.
Synthesis
3-AMINO-2,2-DIMETHYL-PROPANOIC ACID

19036-43-2

Di-tert-butyl dicarbonate

24424-99-5

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

180181-02-6

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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