Hydrogen Peroxide → HCID 52943384, compound

HRID 1594013Notes

Reaction equation

HRID 1594013 reaction equation
B.C1C[O:5]CC1.[CH2:7]([O:9][C:10]([C:12]1[C:13]([C:36]([O:38][CH2:39][CH3:40])=[O:37])=[C:14]([CH2:33][CH:34]=[CH2:35])[N:15]2[C:20]=1[C:19]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)=[CH:18][C:17]([N:27]1[CH2:32][CH2:31][O:30][CH2:29][CH2:28]1)=[N:16]2)=[O:11])[CH3:8].[OH-].[Na+].OO>C1COCC1>[CH2:7]([O:9][C:10]([C:12]1[C:13]([C:36]([O:38][CH2:39][CH3:40])=[O:37])=[C:14]([CH2:33][CH2:34][CH2:35][OH:5])[N:15]2[C:20]=1[C:19]([C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1)=[CH:18][C:17]([N:27]1[CH2:28][CH2:29][O:30][CH2:31][CH2:32]1)=[N:16]2)=[O:11])[CH3:8]

Participants

6

Reactant 4

HCID 784Hydrogen PeroxideHCID 14798Sodium HydroxideHCID 2723981Borane;tetrahydrofuranHCID 25207743HCID 25207743, compound

Product 1

HCID 52943384HCID 52943384, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

BH3.THF (162 μL, 0.162 mmol) was added dropwise via syringe to a solution of 1 (50 mg, 0.108 mmol) in anhydrous THF (6 mL). The reaction mixture was stirred at ambient temperature for 1 h. 5% aqueous NaOH (0.5 mL) and 30% aqueous H2O2 (1 mL) were added and the reaction mixture was stirred at ambient temperature for 1.5 h. The reaction mixture was extracted with EtOAc and the organic layers were pooled, washed with brine, dried (MgSO4), filtered, and concentrated in vacuo to provide a yellow oil. The oil was purified by flash chromatography (silica gel, 40% EtOAc/hexane) to yield a yellow oil. The oil was triturated in (1:1) Et2O/hexane to provide a white solid. 1H NMR (DMSO-d6) δ 0.89 (t, J=7.2 Hz, 3H), 1.21 (t, J=7.0 Hz, 3H), 1.78 (m, 2H), 3.18 (m, 2H), 3.40 (m, 2H), 3.50 (m, 6H), 3.72 (m, 4H), 4.16 (q, J=7.1 Hz, 2H), 4.45 (t, J=5.3 Hz, 1H), 6.77 (s, 1H), 7.41 (m, 2H), 7.46 (m, 3H). Mass Spectrum (ESI+) m/e=482.2 (M+H).

Workup

  1. stirringthe reaction mixture was stirred at ambient temperature for 1.5 h
  2. extractionThe reaction mixture was extracted with EtOAc
  3. washwashed with brine
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customto provide a yellow oil
  8. customThe oil was purified by flash chromatography (silica gel, 40% EtOAc/hexane)
  9. customto yield a yellow oil
  10. customThe oil was triturated in (1:1) Et2O/hexane
  11. customto provide a white solid

Sources & evidence

ORD record
ord-ca4c991c4d594693ac0b2466136a7531
Source dataset
uspto-grants-2007_11
Patent number
US07300932B2

Reaction notes

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