Reaction SMILES: OO.[C:3]([O:22][CH:23]1[CH2:28][C:27]([CH3:30])([CH3:29])[NH:26][C:25]([CH3:32])([CH3:31])[CH2:24]1)(=[O:21])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20].[C:33](=[O:36])(O)[O-].[Na+].S([O-])([O-])=O.[Na+].[Na+]>O.C1CCCCC1.C(#N)C.C(OCC)(=O)C.C(O)(=O)C>[CH:33]1([O:36][N:26]2[C:27]([CH3:30])([CH3:29])[CH2:28][CH:23]([O:22][C:3](=[O:21])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20])[CH2:24][C:25]2([CH3:31])[CH3:32])[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]1
Reactant: O=C([O-])O
Reactant: CCCCCCCCCCCCCCCCCC(=O)OC1CC(C)(C)NC(C)(C)C1
Agent: O=S([O-])[O-]
Agent: OO
Agent: [Na+]
Solvent: O
Solvent: CCOC(C)=O
Solvent: C1CCCCC1
Product: CCCCCCCCCCCCCCCCCC(=O)OC1CC(C)(C)N(OC2CCCCC2)C(C)(C)C1
Temperature: 65 °C
Reaction time: 4.5 h
Yield: 846.8 %

Procedure:
A solution of 2.84 g (41.7 mmol) of 50% aqueous hydrogen peroxide is added dropwise over 3 hours to a mixture of 5.98 g (14.1 mmol) of 4-octadecanoyloxy-2,2,6,6-tetramethylpiperidine, 0.026 g (0.31 mmol, 2.2 mole percent) of sodium bicarbonate dissolved in 0.6 g of water, 4 ml of cyclohexane, and 4 ml of acetonitrile while the reaction temperature is maintained at 65-68° C. After the peroxide is added, the reaction mixture is stirred at 65° C. for 4.5 hours. The red mixture is cooled, and then diluted with cyclohexane and acetonitrile. The aqueous layer is discarded. The mixture is washed with water, and the wash is extracted with a mixture of cyclohexane and acetonitrile. A total of 25 ml each of cyclohexane and acetonitrile are used in the work up. The organic layers are combined, and more acetonitrile (13 ml) is added. The temperature is brought to 50° C., and a solution of 0.117 g (0.433 mmol) of ferric chloride hexahydrate and 0.096 g (1.60 mmol) of glacial acetic acid in 2 ml of water is added to the reaction mixture. A solution of 4.28 g (63 mmol) of 50% aqueous peroxide is added dropwise over 3 hours to the reaction mixture while the temperature is maintained near 60° C. A solution of 0.042 g of ferric chloride hexahydrate, 0.5 g of water, and 0.044 g of glacial acetic acid is added to the reaction mixture 1.5 hours after the peroxide addition is begun. The mixture is heated at reflux for 4 hours after the peroxide is added, then allowed to stand at room temperature overnight. Glacial acetic acid (0.403 g, 6.7 mmol) and a solution of 0.130 g of ferric chloride hexahydrate in 0.5 g of water are added to the red reaction mixture. The temperature is brought to reflux, and a solution of 4.56 g (67.0 mmol) of 50% aqueous hydrogen peroxide is added dropwise over 2 hours. A solution of 0.070 g of ferric chloride hexahydrate and 0.096 g of glacial acetic acid in 1 ml of water is added to the reaction mixture 1 hour after the peroxide addition is begun. The mixture is heated at reflux for 2.5 hours after the peroxide is added. The mixture is cooled and stirred with 10 ml of 10% aqueous sodium sulfite. Ethyl acetate is added, and the aqueous layer is extracted with ethyl acetate. The organic layers are combined and concentrated. The concentrate is purified by flash chromatography with 20:1 heptane-ethyl acetate to afford a red liquid. A second purification by flash chromatography affords 1.37 g (19% yield) of the title compound as a white solid, mp 42-45. The assay is % by NMR integration.