Oxazole, 2-[[[(1,1-dimethylethyl)dimethylsilyl]oxy]methyl]- synthesis

Yield:1163254-82-7 92.8%

Reaction Conditions:

with 1H-imidazole in tetrahydrofuran at 0; for 5 h;

Steps:

A692.1 Synthesis of (3S)-1-(4-(dimethylamino)-4-methylpent-2-ynoyl)-N-((2S)-1-(((63S,4S)-11-ethyl-12-(2-((S)-1-methoxyethyl)pyridin-3-yl)-10,10-dimethyl-5,7-dioxo-61,62,63,64,65,66-hexahydro-11H-8-oxa-2(5,2)-oxazola-1(5,3)-indola-6(1,3)-pyridazinacycloundecaphane-4-yl)amino)-3-methyl-1-oxobutan-2-yl)-N-methylpyrrolidine-3-carboxamide

Step 1.
To a solution of 1,3-oxazol-2-ylmethanol (5.0 g, 50.46 mmol) in THF (75 mL), were added imidazole (8.59 mg, 0.13 mmol), and TBSCl (11.41 mg, 0.08 mmol) at 0° C.
The resulting solution was stirred for 5 h then concentrated under reduced pressure.
The crude material was purified by silica gel column chromatography to afford 2-[[(tert-butyldimethylsilyl)oxy]methyl]-1,3-oxazole (10 g, 92.8% yield) as colorless oil. LCMS (ESI): m/z [M+H] calc'd for C₁₀H₁₉NO₂Si 214.13; found 214.3.

References:

US2021/130303,2021,A1 Location in patent:Paragraph 1468-1469