C(=O)([O-])[O-].[K+].[K+].[C:7]([C:9]([NH:12][S:13]([C:15]([CH3:18])([CH3:17])[CH3:16])=[O:14])([CH3:11])[CH3:10])#[N:8].Cl.[NH2:20][OH:21]>CCO>[CH3:16][C:15]([CH3:18])([S:13]([NH:12][C:9]([CH3:11])([CH3:10])[C:7](=[N:20][OH:21])[NH2:8])=[O:14])[CH3:17]Potassium carbonate (2.94 g, 21.2 mmol) was added to a stirring solution of N-(2-cyanopropan-2-yl)-2-methylpropane-2-sulfinamide (1.0 g, 5.3 mmol) and hydroxylamine hydrochloride (738 mg, 10.6 mmol) in EtOH (18 mL) at rt. The reaction was heated to 60° C. for 16 h. The reaction was then concentrated and the resulting residue was diluted with EtOAc and washed with water, and sat NaCl aq. The organic phase was dried over Na2SO4, filtered and concentrated azeotroping with toluene to give the expected product 2-(1,1-dimethylethylsulfinamido)-N′-hydroxy-2-methylpropanimidamide (1.0 g, 4.5 mmol, 85% yield) as a white solid consistent by LCMS and NMR. LC-MS retention time: 0.35 min; m/z (MH+): 222. 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 10% acetonitrile/90% H2O/0.1% trifluoroacetic acid and solvent B was 10% H2O/90% acetonitrile/0.1% trifluoroacetic acid. MS data was determined using a Micromass Platform for LC in electrospray mode. 1H NMR (400 MHz, DMSO-d6) δ 9.14 (s, 1H), 5.27 (s, 1H), 5.25 (s, 2H), 1.36 (d, J=5.0 Hz, 6H), 1.12 (s, 9H).
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