Adding a certain compound to certain chemical reactions, such as: 61644-18-6, name is Chloromethyl isobutyrate, belongs to esters-buliding-blocks compound, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 61644-18-6, HPLC of Formula: C5H9ClO2
A solution of compound Int-1 (100 mg, 0.239 mmol) in 1.2 mL of acetonitrile, was treated with potassium carbonate (99 mg, 0.717 mmol), potassium iodide (119 mg, 0.717 mmol), 18-crown-6 (3.16 mg, 0.012 mmol) followed by chloromethyl isobutyrate (65.3 mg, 0.478 mmol). The reaction mixture was stirred at 80C for 16 h. The resulting mixture was cooled to room temperature, and partitioned between ethyl acetate and water. The aqueous phase was back extracted with ethyl acetate and the combined organic layers were dried over Na2S04, filtrered, and concentrated in vacuo. The residue was purified on a XBridge1M C18, 30×250 mm column, eluting with acetonitrile / water (5 mM NH4HCO3) at 50 mL / min using a 20 min 20-90% acetonitrile / water gradient. Clean fractions were partitioned between water and (0266) dichloromethane. The organic phase was dried over Na2S04, filtered and concentrated to give compound 14. (0267) Compound 14: 1H MR (500 MHz, DMSO-i4) delta 10.30 (t, J= 5.9 Hz, 1H), 8.55 (s, 1H), 7.40 (td, J= 8.7, 6.6 Hz, 1H), 7.23 (td, J= 10.0, 2.6 Hz, 1H), 7.05 (td, J= 8.6, 2.5 Hz, 1H), 5.84 – 5.61 (m, 2H), 4.63 (dd, J= 14.4, 2.2 Hz, 1H), 4.58 – 4.46 (m, 3H), 3.89 (m, 1H), 3.87 – 3.76 (m, 1H), 3.44 (m, 1H), 2.45 (m, 1H), 2.23 (d, J= 10.2 Hz, 1H), 1.48 – 1.30 (m, 3H), 1.11 (s, 3H), 1.04 (d, J= 7.0 Hz, 6H). LCMS M+l = 519.3.
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Reference:
Patent; MERCK SHARP & DOHME CORP.; YU, Tao; MCCAULEY, John, A.; WHITEHEAD, Alan; APGAR, James, M.; RAHEEM, Izzat, T.; DONG, Guizhen; WADDELL, Sherman, T.; LI, Hong; (43 pag.)WO2018/140368; (2018); A1;,
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