Electric Literature of 133803-81-3 ,Some common heterocyclic compound, 133803-81-3, molecular formula is C11H22O5, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc., below Introduce a new synthetic route.
To a solution of tert- butyl 3-[2-(2-hydroxyethoxy)ethoxy]propanoate (350 mg, 1.49 mmol) in DCM (15 ml) was added TEA (0.62 ml, 4.48 mmol), then the reaction mixture was cooled to 0 C (water ice/acetone bath) and Mesyl chloride (0.14 ml, 1.79 mmol) was added dropwise. The reaction mixture was stirred for 1 h at room temperature. By TLC no starting material (Hex:AcOEt, 3:7). Reaction mixture was poured into an aqueous solution of NaHC03 (20 mL) and product extracted with DCM (20mL, 2x), the organic extracts were combined, dried (Na2S04), and evaporated under vacuum. The crude product (mesylate) was used in the next step without any further purification (>95% pure by NMR): 1H NMR (500 MHz, Chloroform-d) delta 4.44 – 4.28 (m, 2H), 3.76 (dd, J = 5.2, 3.8 Hz, 2H), 3.70 (t, J = 6.4 Hz, 2H), 3.68 – 3.57 (m, 4H), 3.07 (s, 3H), 2.49 (t, J = 6.4 Hz, 2H), 1.45 (s, 9H). [00400] Crude mixture from previous step was diluted in Acetonitrile (5 ml) and Nal (335.88 mg, 2.24 mmol) was added, the reaction mixture was stirred at 70 C for 12 h (overnight). By TLC no starting material (Hex:AcOEt, 7:3), the reaction was poured into an aqueous solution of Na2S203 (10%, 50 mL) and product was extracted with DCM (2×50 mL). Organic extracts were combined, dried (Na2S04) and evaporated under vacuum. Crude product was purified by flash chromatography (SiO2-40g, grad. Hex:AcOEt, 2 to 40% in 15 min), to give 413 mg of product as an oil (80% yield). 1H NMR (500 MHz, Chloroform-d) delta 3.73 (dt, J = 13.5, 6.6 Hz, 4H), 3.68 – 3.54 (m, 4H), 3.24 (t, J = 6.9 Hz, 2H), 2.50 (t, J = 6.5 Hz, 2H), 1.44 (s, 9H). 13C NMR (151 MHz, cdcl3) delta 171.00, 80.69, 72.11, 70.50, 70.27, 67.09, 36.39, 28.25, 3.02. LC- MS ESI); m/z: [M+Na]+ Calcd. for CnH2iI04Na, 367.0382. Found 367.0943.
In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles. 133803-81-3, tert-Butyl 3-(2-(2-hydroxyethoxy)ethoxy)propanoate, other downstream synthetic routes, hurry up and to see.
Reference:
Patent; ARVINAS, INC.; YALE UNIVERSITY; CREW, Andrew P.; DONG, Hanqing; WANG, Jing; CREWS, Craig M.; JAIME-FIGUEROA, Saul; (496 pag.)WO2018/226542; (2018); A1;,
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