With the rapid development and complex challenges of chemical substances, the synthesis of new drugs is usually one of the most effective ways to increase yield.30379-58-9, name is Benzyl 2-hydroxyacetate, molecular formula is C9H10O3, molecular weight is 166.17, as common compound, the synthetic route is as follows.SDS of cas: 30379-58-9
(S)-l -benzyl 2-methyl aziridine-l,2-dicarboxylate (5.105 g, 21.70 mmol), and benzyl 2-hydroxyacetate (6.16 ml, 43.4 mmol) were dissolved in DCM (43.4 ml) and cooled to 0C followed by the addition of BF3.0Et2 (0.275 ml, 2.170 mmol). The reaction was stirred for 2 h. TLC showed the aziridine starting material to be consumed. The reaction was stirred for and additional 14 h. Saturated sodium bicarbonate solution was added to the reaction and the biphasic mixture was vigorously stirred for 20 min. The reaction was diluted with DCM and separated from the aquious phase. The organic layer was washed with brine, dried over sodium sulate and concentrated under vacuum. The crude material was purified by flash chromatography using 10-40% EtOAc/Hexanes. The product fractions were collected and the solvent removed under vacuum to give methyl 0-(2-(benzyloxy)-2-oxoethyl)-N-((benzyloxy)carbonyl)-L-serinate, 3.0 (34%). ESI-MS(+) m/z 402.1 (M+l). NMR (400MHz, CHLOROFORM-d) d 7.43 – 7.30 (m, 10H), 5.95 (d, J=8.0 Hz, IH), 5.18 (s, 2H), 5.15 (s, 2H), 4.50 (dt, J=8.4, 3.1 Hz, IH), 4.12 (d, J=2.8 Hz, 2H), 4.10 – 4.04 (m, IH), 3.81 (dd, J=9.4, 3.1 Hz, IH), 3.77 (s, 3H).
At the same time, in my other blogs, there are other synthetic methods of this type of compound,30379-58-9, Benzyl 2-hydroxyacetate, and friends who are interested can also refer to it.
Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; SUN, Li-Qiang; ZHAO, Qian; MULL, Eric; GILLIS, Eric P.; SCOLA, Paul Michael; (290 pag.)WO2016/57624; (2016); A1;,
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