Yield:132684-09-4 92%

Reaction Conditions:

with sodium hydride in 1,4-dioxane;mineral oil;

Steps:

3 Synthesis of UI-EP001 (8)

di-tert-butyl 3, 6, 9, 12 - tetraoxatetradecanedioate (1). A mixture of triethylene glycol (1.50 g, 1.36 ml, 10 mmol, 1 eq.), NaH 60% in mineral oil (800 mg, 20 mmol, 2 eq.) and tert-Butyl bromoacetate (4.50 g, 3.4 ml, 20 mmol, 2 eq.) were dissolved in 10 mL of dioxane. Reaction mixture was stirred overnight, followed by quenching with saturated NH₄CI. The mixture was extracted with EtOAc and dried by N 82804, then concentrated in vacuum. The product was applied to flash chromatography (Hexane:EtOAc = 8:2) to give compound 1 an colorless oil. Yield: 3.25 g, 8.60 mmol (92%). ¹H NMR (300 MHz, CDCI₃): 6 3.99 (s, 4H), 3.72-3.66 (m, 16H), 1.46 (s, 9H). HRMS (ESI+) cald for C₁₈H₃₄O₈ [M + 1]⁺: 379.23, found 379.46.

References:

WO2021/217036,2021,A1 Location in patent:Page/Page column 47