Potassium Phosphate, Dibasic → Benzyl ((3S,4R)-2-oxo-4-((2-oxooxazolidin-3-yl)methyl)azetidin-3-yl)carbamate

Participants

Reaction Conditions

Reaction Steps

Prepared in an analogous manner to example 4, step 2 using benzyl ((3S,4R)-1-(2,4-dimethoxybenzyl)-2-oxo-4-((2-oxooxazolidin-3-yl)methyl)azetidin-3-yl)carbamate (3.84 g, 8.18 mmol), K2S2O8 (3.10 g, 11.5 mmol) and K2HPO4 (1.852 g, 10.6 mmol) in ACN:water (2:1, 136 mL) while heating for 40 min at 90° C. More K2S2O8 (663 g, 2.45 mmol) and K2HPO4 (370 mg, 2.13 mmol) were added and it was heated for another 3 h. More K2S2O8 (332 mg, 1.23 mmol) and K2HPO4 (185 mg, 1.06 mmol) were added, and it was heated for an additional 2 h, whereupon it was concentrated in vacuo, removing most of the ACN. The mixture was diluted with brine/EtOAc and the layers were separated. The aqueous layer was extracted with EtOAc (3×) and the combined organic layers were dried over Na2SO4. The crude residue was purified via silica gel chromatography (EtOAc-Heptane, 0-100% then MeOH-DCM, 10%) to afford the title compound (1.61 g, 62%) as a beige foam. LCMS: Rt=0.51 min, m/z=320.0 (M+1) Method 2m_acidic.

Provenance & Evidence