Sodium Chlorite → HCID 89662736, compound

HRID 1479023Notes

Reaction equation

HRID 1479023 reaction equation
Cl([O-])=O.[Na+].P([O-])(O)(O)=[O:6].[Na+].[C:11]([O:15][C:16]([N:18]1[CH:24]([C:25]([F:28])([F:27])[F:26])[CH2:23][CH2:22][N:21]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=2[CH:35]=[O:36])[CH2:20][CH2:19]1)=[O:17])([CH3:14])([CH3:13])[CH3:12]>O.O1CCOCC1>[C:11]([O:15][C:16]([N:18]1[CH:24]([C:25]([F:28])([F:27])[F:26])[CH2:23][CH2:22][N:21]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=2[C:35]([OH:6])=[O:36])[CH2:20][CH2:19]1)=[O:17])([CH3:14])([CH3:12])[CH3:13]

Participants

6

Reactant 3

HCID 23668197Sodium ChloriteHCID 23672064Monosodium phosphateHCID 131736544HCID 131736544, compound

Product 1

HCID 89662736HCID 89662736, compoundYield 84%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution of sodium chlorite (214 mg; 2.36 mmol; 5.5 eq.) and sodium dihydrogenphosphate (186 mg; 1.55 mmol; 3.6 eq.) in water (2 mL) was added dropwise to a mixture of 4-(2-formyl-phenyl)-7-trifluoromethyl-[1,4]diazepane-1-carboxylic acid tert-butyl ester (160 mg; 0.43 mmol; 1 eq.) in 1,4-dioxane (2 mL). The reaction mixture was stirred at room temperature for 1 hour and the 1,4-dioxane concentrated in vacuo. The aqueous solution was diluted with water, the pH made acidic with 0.1M HCl and extracted with EA (2×). The combined organic layer was washed with brine, dried over magnesium sulfate and concentrated in vacuo to afford the title compound (140 mg, 84%) as a yellow solid. UPLC/MS: (MS+) 389.2 ([M+H]+).

Workup

  1. concentrationthe 1,4-dioxane concentrated in vacuo
  2. additionThe aqueous solution was diluted with water
  3. extractionextracted with EA (2×)
  4. washThe combined organic layer was washed with brine
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-5058ae34a1174149bb417d5962803edb
Source dataset
uspto-grants-2016_08
Patent number
US09403835B2

Reaction notes

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