Application of 15441-07-3, These common heterocyclic compound, 15441-07-3, name is Methyl 3-(chlorosulfonyl)propanoate, 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 Compound IE (40 mg, 0.092 mmol) and triethylamine (0.026 mL, 0.184 mmol) in CH2CI2 (1 mL) in an ice bath was added methyl 3- (chlorosulfonyl)propanoate (25.7 mg, 0.138 mmol). Upon completion of addition, the reaction mixture was stirred in the ice bath for 15 min. After this time, the reaction mixture was allowed to warm to rt, where it stirred for 3 h. At the conclusion of this period, the reaction mixture was quenched with saturated aq aHCOs (1 mL) and then extracted with CH2CI2 (3 x 2 mL). The combined organic layers were dried( a2S04), filtered, and concentrated to yield a residue. The residue was purified by column chromatography (silica gel, CELC^-EtOAc gradient 0 to 90% EtOAc) to afford Example 2 as a white solid (42 mg, 78% yield). XH NMR (500 MHz, DMSO- d6) delta ppm 8.24 (2H, s), 7.98 (IH, d, J=1.9 Hz), 7.64 (IH, d, J=8.5 Hz), 7.51 (IH, dd, J=8.5, 1.9 Hz), 6.20 – 6.26 (IH, m), 5.36 – 5.44 (IH, m), 4.15 – 4.23 (2H, m), 3.91 – 3.95 (2H, m), 3.62 (3H, s), 3.51 – 3.59 (2H, m), 3.46 (2H, t, J=5.6 Hz), 3.40 (2H, t, J=7.2 Hz), 2.74 (2H, t, J=7.2 Hz), 2.57 – 2.66 (2H, m), 2.38 (2H, t, J=7.4 Hz), 2.09 – 2.19 (2H, m), 1.70 – 1.81 (2H, m), 1.47 – 1.58 (2H, m), 0.88 (3H, t, J=7.3 Hz).LC/MS (m/z) = 586 (M+H)+.
The synthetic route of 15441-07-3 has been constantly updated, and we look forward to future research findings.
Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; YE, Xiang-Yang; WACKER, Dean A.; ROBL, Jeffrey A.; WANG, Ying; WO2011/140160; (2011); A1;,
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