A common heterocyclic compound, 90030-48-1, name is Sodium 3-methoxy-3-oxopropane-1-sulfinate, molecular formula is C4H7NaO4S, 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. 90030-48-1.
Methyl 3 -( 1 -((2-(trimemylsilyl)ethoxy)methyl)- 1 H-pyrrolo [2,3 -b]pyridin-5- ylsulfonvDpropanoate (4-lb) To a nitrogen gas purged sealable vial of 5-bromo-l-((2-( methylsilyl)ethoxy)methyl)-lH-pyrrolo[2,3-b]pyridine 4-la (3000 mg, 9.17 mmol), copper(i) iodide (6983 mg, 36.7 mmol) and sodium 3-methoxy-3-oxopropane-l-sulfinate(TYGER) (6385 mg, 36.7 mmol) was added DMSO (15 ml) . The reaction mixture was heated in an oil bath at 105c for 18hrs. LCMS analysis showed reaction to be a mixture of desired ester and acid. The reaction was quenched into ethyl acetate (200 ml) and water (200 ml) and the ph adjusted from 7 to 3 with IN HC1. The reaction was filtered thru celite and sand and the filtrate layers separated. The organic which contained a mix of acid and ester was dried over sodium sulfate, filtered and concentrated to an oil. The oil was azeotroped with toluene to remove any remaining water to give a brown oil, 3.4 gms. The oil was dissolved in dichloromethane (20 ml) and methanol (20.00 ml) cooled to 0C and TMS-Diazomethane (4.94 ml, 9.88 mmol) slowly added dropwise. The reaction was stirred at 0C for 10 minutes, quenched with aq. KHSO4 and allowed to stir at room temperature for 1 hr. The reaction was concentrated to remove methanol and the product extracted into ethyl acetate (100 ml), dried over sodium sulfate and concentrated to oil . The oil was chromatographed on silica (100 g, 0-50% ethyl acetate/hexanes) to give the product 4-lb as oil, 1.46 g . LRMS (ESI) m/z 399.1 [(M+H)+; calcd for C17H26N205SSi: 399.1 ].
The synthetic route of Sodium 3-methoxy-3-oxopropane-1-sulfinate has been constantly updated, and we look forward to future research findings.
Reference:
Patent; MERCK SHARP & DOHME CORP.; BUTCHER, John, W.; WITTER, David; DINSMORE, Christopher; KIM, June; HENDRIX, John; ARCHARYA, Raksha; AHEARN, Sean, P.; JUNG, Joon; RIVKIN, Alexey; JONES, Philip; WO2013/52355; (2013); A1;,
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