Hydrogen Peroxide → HCID 89555370, compound

HRID 2203421Notes

Reaction equation

HRID 2203421 reaction equation
CC1(C)C(C)(C)OB([C:9]2[CH:10]=[CH:11][C:12]3[O:16][N:15]=[C:14]([N:17]([C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[C:13]=3[CH:32]=2)O1.[OH:34]O>O1CCCC1>[OH:34][C:9]1[CH:10]=[CH:11][C:12]2[O:16][N:15]=[C:14]([N:17]([C:25]([O:27][C:28]([CH3:29])([CH3:31])[CH3:30])=[O:26])[C:18]([O:20][C:21]([CH3:22])([CH3:23])[CH3:24])=[O:19])[C:13]=2[CH:32]=1

Participants

4

Reactant 2

HCID 784Hydrogen PeroxideHCID 89555360HCID 89555360, compound

Product 1

HCID 89555370HCID 89555370, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of di-tert-butyl [5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,2-benzoxazol-3-yl]imidodicarbonate (0.81 g, 1.8 mmol) in tetrahydrofuran (15 mL) was added 30% w/v aqueous hydrogen peroxide (0.75 mL, 7.0 mmol). The mixture was stirred at ambient temperature for 18 h and concentrated in vacuo. The residue was taken up in ethyl acetate (20 mL), washed with water (2×15 mL), dried over anhydrous sodium sulfate, filtered and concentrated in vacuo to afford di-tert-butyl (5-hydroxy-1,2-benzoxazol-3-yl)imidodicarbonate as a colorless solid in quantitative yield (0.65 g): 1H NMR (300 MHz, CDCl3) δ7.46-7.43 (m, 1H), 7.12-7.09 (m, 1H), 6.86-6.85 (m, 1H), 1.39-1.36 (m, 9H), 1.26-1.21 (m. 9H); MS (ES+) m/z 350.9 (M+1).

Workup

  1. concentrationconcentrated in vacuo
  2. washwashed with water (2×15 mL)
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-ae04bc67897a4c4e950ee57e3a404de2
Source dataset
uspto-grants-2016_06
Patent number
US09365578B2

Reaction notes

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