ChemicalBook CAS DataBase List t-Boc-N-Amido-PEG3-propargyl

t-Boc-N-Amido-PEG3-propargyl synthesis

8synthesis methods

Product Name:t-Boc-N-Amido-PEG3-propargyl
CAS Number:1333880-60-6
Molecular formula:C14H25NO5
Molecular Weight:287.35

(2-[2-(2-HYDROXY-ETHOXY)-ETHOXY]-ETHYL)-CARBAMIC ACID TERT-BUTYL ESTER

139115-92-7
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106-96-7 Synthesis

106-96-7
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1333880-60-6
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Yield:1333880-60-6 72%

Reaction Conditions:

with tetra-(n-butyl)ammonium iodide;potassium iodide;potassium hydroxide in tetrahydrofuran at 25; for 16 h;Inert atmosphere;

Steps:

Tert-butyl N-[2-[2-(2-prop-2-ynoxyethoxy)ethoxy]ethyl]carbamate (Intermediate VS)
A mixture of tert-butyl N-[2-[2-(2-hydroxyethoxy)ethoxy]ethyl]carbamate (3.00 g, 12.0 mmol), 3-bromoprop-1-yne (1.72 g, 14.4 mmol, 1.24 mL), TBAI (356 mg, 962 umol), KI (299 mg, 1.81 mmol) and KOH (675 mg, 12.0 mmol) in THF (30 mL) was degassed and purged with N₂for 3 times, and then the mixture was stirred at 25° C. for 16 hrs under N₂atmosphere. On completion, the mixture was filtered and the filtrate was concentrated in vacuo. The residue was purified by silica gel chromatography to give the title compound (2.50 g, 72% yield) as light yellow oil. ¹H NMR (400 MHz, CDCl₃) δ 5.05 (s, 1H), 4.22 (d, J=2.4 Hz, 2H), 3.76-3.60 (m, 8H), 3.55 (t, J=5.2 Hz, 2H), 3.35-3.27 (m, 2H), 2.44 (t, J=2.4 Hz, 1H), 1.47 (s, 9H).

References:

Kymera Therapeutics, Inc.;Mainolfi, Nello;Ji, Nan;Kluge, Arthur F.;Weiss, Matthew M.;Zhang, Yi US2019/192668, 2019, A1 Location in patent:Paragraph 4042; 4043

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