Acetic Acid → HCID 131732506, compound

Participants

Reaction Steps

(Z)-2-(1,1-dimethylethylsulfinamido)-N′-hydroxy-2-methylpropanimidamide (140 mg, 0.633 mmol) in AcOH (4 ml) was treated with [diethoxy(2H)methoxy]ethane (0.106 ml, 0.633 mmol) at rt. The reaction was allowed to stir at rt for 16 h. LCMS showed a major peak with the expected M+H. The reaction was concentrated to dryness azeotroping with toluene 3×. The resulting oil was purified on silica gel (Biotage, EtOAc/hexanes gradient (Rf ˜0.2 in 70% EtOAc/Hex, visualized with permanganate stain), to give the expected product (27 mg, 0.12 mmol, 18% yield) consistent by LCMS. LC-MS retention time: 1.47 min; m/z (MH+): 233. LC data was recorded on a Shimadzu LC-10AS liquid chromatograph equipped with a Phenomenex-Luna 3u C18 2.0×30 mm column using a SPD-10AV UV-Vis detector at a detector wave length of 220 nM. The elution conditions employed a flow rate of 1 mL/min, a gradient of 100% solvent A/0% solvent B to 0% solvent A/100% solvent B, a gradient time of 2 min, a hold time of 1 min, and an analysis time of 3 min where solvent A was 5% MeOH/95% H2O/10 mM ammonium acetate and solvent B was 5% H2O/95% MeOH/10 mM ammonium acetate. MS data was determined using a Micromass Platform for LC in electrospray mode. Step 2: Preparation of the titled compound: 2-[(2H)-1,2,4-oxadiazol-3-yl]propan-2-amine hydrochloride HCl (1.0 mL, 1.9 mmol) (2 M in Et2O) was added to a stirring solution of 2-methyl-N-{2-[(2H)-1,2,4-oxadiazol-3-yl]propan-2-yl}propane-2-sulfinamide (27 mg, 0.12 mmol) in MeOH (1 mL) at rt. The reaction was allowed to stir for 2 h and then concentrated azeotroping with toluene to give the expected product (15 mg, 0.091 mmol, 78% yield) consistent by NMR. 1H NMR (400 MHz, METHANOL-d4) δ 1.77 (s, 6H).

Provenance & Evidence