Sodium Chloride → HCID 42599641, compound

HRID 1898730Notes

Reaction equation

HRID 1898730 reaction equation
[OH:1][C:2]1[C:3]([CH3:27])=[C:4]2[C:9](=[C:10]([CH3:13])[C:11]=1[CH3:12])[O:8][C:7]([CH3:26])([C:14]([NH:16][CH2:17][CH2:18][CH2:19][N:20]1[CH2:25][CH2:24][O:23][CH2:22][CH2:21]1)=[O:15])[CH2:6][CH2:5]2.[O:28]=[N+]([O-])[O-].[O-][N+](=O)[O-].[O-][N+](=O)[O-].[O-][N+](=O)[O-].[O-][N+](=O)[O-].[O-][N+](=O)[O-].[Ce+4].[NH4+].[NH4+].[Na+].[Cl-].C([O-])(O)=O.[Na+]>C(C#N)(C)=O.O.CCOC(C)=O>[OH:28][C:7]([CH3:26])([CH2:6][CH2:5][C:4]1[C:9](=[O:8])[C:10]([CH3:13])=[C:11]([CH3:12])[C:2](=[O:1])[C:3]=1[CH3:27])[C:14]([NH:16][CH2:17][CH2:18][CH2:19][N:20]1[CH2:25][CH2:24][O:23][CH2:22][CH2:21]1)=[O:15]

Participants

9

Reactant 4

HCID 5234Sodium ChlorideHCID 180504Ceric ammonium nitrateHCID 516892Sodium BicarbonateHCID 672629816-hydroxy-2,5,7,8-tetramethyl-N-(3-morpholinopropyl)chroman-2-carboxamide

Product 1

HCID 42599641HCID 42599641, compoundYield 15.3%

Reagents, catalysts & solvents 4

HCID 962WaterCatalystHCID 962WaterSolventHCID 8857Ethyl AcetateSolventHCID 694302-OxopropiononitrileSolvent

Procedure

To a solution of 100 mg (0.266 mmol) of 6-hydroxy-2,5,7,8-tetramethyl-N-(3-morpholinopropyl)chroman-2-carboxamide in 5 mL AcCN and one drop of H2O at 0° C., was added a solution of 320.3 mg CAN (0.584 mmol) in 3 mL H2O dropwise. The solution was treated with 5 mL EtOAc and 5 mL saturated NaCl followed by ˜1 g of NaHCO3 and 1 h of vigorous stirring. The suspension was then extracted 3×5 mL 4:1 isopropyl alcohol:isopropyl acetate solution and the combined organics dried over Na2SO4, concentrated to a yellow oil and flashed chromatographed to yield 16 mg of 2-hydroxy-2-methyl-N-(3-morpholinopropyl)-4-(2,4,5-trimethyl-3,6-dioxocyclohexa-1,4-dienyl)butanamide as a dark yellow oil.

Workup

  1. extractionThe suspension was then extracted 3×5 mL 4:1 isopropyl alcohol
  2. dry with materialisopropyl acetate solution and the combined organics dried over Na2SO4
  3. concentrationconcentrated to a yellow oil
  4. customflashed chromatographed

Sources & evidence

ORD record
ord-f712a60a36444f289b2683f3b349ff48
Source dataset
uspto-grants-2013_08
Patent number
US08519001B2

Reaction notes

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