Hydrogen Peroxide → HCID 70043459, compound

HRID 2209455Notes

Reaction equation

HRID 2209455 reaction equation
[C:1]([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][CH2:15][CH:16]=[C:17]([CH:19]2[CH2:23][CH2:22][NH:21][C:20]2=[O:24])C)[CH2:10][CH2:9]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].CSC.B.[OH-].[Na+].OO.C([O-])([O-])=[O:34].[K+].[K+]>C1COCC1.C(O)C.O>[C:1]([N:8]1[CH2:9][CH2:10][CH:11]([CH2:14][CH2:15][CH2:16][CH2:17][CH2:19][OH:34])[CH2:12][CH2:13]1)([O:3][C:4]([CH3:5])([CH3:6])[CH3:7])=[O:2].[NH:21]1[CH2:22][CH2:23][CH2:19][C:20]1=[O:24]

Participants

9

Reactant 5

HCID 784Hydrogen PeroxideHCID 11430Potassium CarbonateHCID 14798Sodium HydroxideHCID 12423031(Dimethyl sulfide)trihydroboronHCID 86749014HCID 86749014, compound

Product 1

HCID 70043459HCID 70043459, compound

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent3×

Conditions

Temperature
55 °C

Procedure

A solution of 20 (1.20 g, 3.6 mmol) in THF (3 ml) was added to a solution of borane-dimethyl sulfide (3.6 mmol) in 3 ml THF at 0° C. and this was stirred for 2.5 hr at 0° . Then, H2O (0.15 ml), 10N aqueous NaOH solution (0.65 ml), THF (1 ml), and C2H5OH (0.36 ml) were added at 0° and with stirring the reaction mixture was warmed to 23° and treated with 30% H2O2 (0.36 ml). This solution was heated to 55° C. and stirred for 2 hours. The reaction mixture was cooled, saturated with K2CO3 an the organic phase was separated, dried (MgSO4) and the solvent removed. The resulting residue was purified by flash chromatography on silica gel eluting with 10% MeOH/EtOAc to give 95. Rf 0.3 (silica gel, 10% MeOH/EtOAc.

Workup

  1. stirringwith stirring the reaction mixture
  2. temperaturewas warmed to 23°
  3. stirringstirred for 2 hours
  4. customwas separated
  5. dry with materialdried (MgSO4)
  6. customthe solvent removed
  7. customThe resulting residue was purified by flash chromatography on silica gel eluting with 10% MeOH/EtOAc

Sources & evidence

ORD record
ord-4c57489a197f4a648a031bd837ba0564
Source dataset
uspto-grants-1995_10
Patent number
US05455243

Reaction notes

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