Methyl 3-(tert-butoxycarbonylaMino)propanoate

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Methyl 3-(tert-butoxycarbonylaMino)propanoate Basic information
Product Name:Methyl 3-(tert-butoxycarbonylaMino)propanoate
Synonyms:Methyl 3-(tert-butoxycarbonylaMino)propanoate;Methyl 3-(Boc-amino)propanoate;methyl3-[(2-methylpropan-2-yl)oxycarbonylamino]propanoate;3-((tertbutyloxycarbonyl)amino)propanoic acidmethyl ester
CAS:42116-55-2
MF:C9H17NO4
MW:203.24
EINECS:
Product Categories:
Mol File:42116-55-2.mol
Methyl 3-(tert-butoxycarbonylaMino)propanoate Structure
Methyl 3-(tert-butoxycarbonylaMino)propanoate Chemical Properties
Boiling point 292.4±23.0 °C(Predicted)
density 1.053±0.06 g/cm3(Predicted)
storage temp. 2-8°C
pka11.82±0.46(Predicted)
AppearanceColorless to light yellow Liquid
Safety Information
MSDS Information
Methyl 3-(tert-butoxycarbonylaMino)propanoate Usage And Synthesis
Synthesis
Di-tert-butyl dicarbonate

24424-99-5

Methyl 3-(tert-butoxycarbonylaMino)propanoate

42116-55-2

General procedure for the synthesis of methyl 3-((tert-butoxycarbonyl)amino)propanoate from di-tert-butyl dicarbonate: β-alanine methyl ester hydrochloride (9.90 g, 70.93 mmol) was suspended in 200 mL of acetonitrile and triethylamine (10 mL, 72.14 mmol) was added. The reaction mixture was stirred at room temperature for 0.3 h. Subsequently, di-tert-butyl dicarbonate (15.48 g, 70.93 mmol) and zirconium(IV) chloride (1.65 g, 7.09 mmol) were added sequentially. The reaction mixture was continued to be stirred at room temperature for 2 hours. After completion of the reaction, the solvent was removed by rotary evaporation. The residue was extracted with ethyl acetate and water, the organic phase was separated and dried over anhydrous sodium sulfate. The dried organic phase was concentrated under reduced pressure to give the target product in a yield of 12.50 g with 87% yield.

References[1] Patent: US2007/238730, 2007, A1. Location in patent: Page/Page column 22
[2] Patent: US2007/259855, 2007, A1. Location in patent: Page/Page column 24
[3] Organic Letters, 2006, vol. 8, # 14, p. 2993 - 2996
[4] Bioorganic and Medicinal Chemistry Letters, 1998, vol. 8, # 13, p. 1607 - 1612
[5] Journal of Medicinal Chemistry, 1991, vol. 34, # 1, p. 73 - 78
Methyl 3-(tert-butoxycarbonylaMino)propanoate Preparation Products And Raw materials
Raw materialsDi-tert-butyl dicarbonate-->Methyl 3-aminopropionate hydrochloride-->Triethylamine-->Acetonitrile
Preparation Products(3-Oxo-propyl)-carbamic acid tert-butyl ester-->Methyl 3-((tert-butoxycarbonyl)aMino)-2,2-diMethylpropanoate
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