ChemicalBook CAS DataBase List N-(tert-Butoxycarbonyl)-L-alanine

N-(tert-Butoxycarbonyl)-L-alanine synthesis

5synthesis methods

Product Name:N-(tert-Butoxycarbonyl)-L-alanine
CAS Number:15761-38-3
Molecular formula:C8H15NO4
Molecular Weight:189.21

56-41-7 Synthesis

56-41-7
772 suppliers
$5.00/5g

24424-99-5 Synthesis

24424-99-5
816 suppliers
$13.50/25G

15761-38-3
512 suppliers
$5.00/10g

Yield:15761-38-3 100%

Reaction Conditions:

with sodium hydroxide in tetrahydrofuran;water at 20; for 17 h;

Steps:

4.2 Step 2 (S)-2-((tert-butoxycarbonyl)amino)propanoic acid
To a suspension of (S)-2-aminopropanoic acid (10.00 g, 112.24 mmol) in H₂O (56 mL) was added NaOH (6.73 g, 168.36 mmol) at 0° C., followed by adding 56 mL of THF and (Boc)₂O (31.85 g, 145.91 mmol) via funnel. The resulted solution was stirred at rt for 17 hours, and extracted with petroleum ether (100 mL×2). The aqueous layer was acidified to pH=1 with 4 M HCl aqueous solution, then was extracted with EtOAc (100 mL×4). The combined organic phase was washed with 100 mL of saturated brine, dried over anhydrous Na₂SO₄, and concentrated in vacuo to give the title compound as colorless oil that was used for the next step without further purification (21.2 g, 100%). [0537] ¹H NMR (600 MHz, CDCl₃) δ (ppm): 9.95 (br. s, 1H), 5.19-5.18 (d, J=5.5 Hz, 1H), 4.32-4.31 (m, 1H), 1.41 (s, 9H), 1.41-1.39 (d, J=7.8 Hz, 3H).

References:

CALITOR SCIENCES, LLC;SUNSHINE LAKE PHARMA CO., LTD.;Xi, Ning;Wang, Liang;Wang, Tingjin US2015/87658, 2015, A1 Location in patent:Paragraph 0536; 0537

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28875-17-4 Synthesis