Hydrogen Peroxide → HCID 58052573, compound

HRID 2190175Notes

Reaction equation

HRID 2190175 reaction equation
[CH3:1][NH:2][C:3]([C:5]1[C:13]2[CH:12]=[C:11]3[C:14](=[CH2:23])[CH2:15][CH2:16][CH2:17][N:18]([S:19]([CH3:22])(=[O:21])=[O:20])[C:10]3=[N:9][C:8]=2[O:7][C:6]=1[C:24]1[CH:29]=[CH:28][C:27]([F:30])=[CH:26][CH:25]=1)=[O:4].CNC(C1C2C=C3C(C)=CCCN(S(C)(=O)=O)C3=NC=2OC=1C1C=CC(F)=CC=1)=[O:34].B.C1COCC1.C1COCC1.[OH-].[Na+].OO>CCOC(C)=O>[CH3:1][NH:2][C:3]([C:5]1[C:13]2[CH:12]=[C:11]3[C:14]([OH:34])([CH3:23])[CH2:15][CH2:16][CH2:17][N:18]([S:19]([CH3:22])(=[O:21])=[O:20])[C:10]3=[N:9][C:8]=2[O:7][C:6]=1[C:24]1[CH:29]=[CH:28][C:27]([F:30])=[CH:26][CH:25]=1)=[O:4]

Participants

8

Reactant 6

HCID 784Hydrogen PeroxideHCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 2723981Borane;tetrahydrofuranHCID 58052304HCID 58052304, compoundHCID 66663321HCID 66663321, compound

Product 1

HCID 58052573HCID 58052573, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
5 °C

Procedure

To a mixture of 2-(4-fluoro-phenyl)-9-methanesulfonyl-5-methylene-6,7,8,9-tetrahydro-5H-1-oxa-9,10-diaza-cyclohepta[f]indene-3-carboxylic acid methylamide and 2-(4-fluoro-phenyl)-9-methanesulfonyl-5-methyl-8,9-dihydro-7H-1-oxa-9,10-diaza-cyclohepta[f]indene-3-carboxylic acid methylamide (30 mg) was added solution of BH3.THF in THF (1 M, 0.14 ml, 2 eq.) at 0° C. The mixture was stirred at 5° C. for 16 h. NaOH (10% aq. solution, 2 eq.) and H2O2 (30% aq. solution, 0.030 ml, 4 eq.) were slowly added. The mixture was stirred at rt for 2 h. The reaction mixture was then diluted with EtOAc and the layers were separated. The aqueous phase was extracted with EtOAc. The combined organic phases were washed with brine, dried (Na2SO4), and concentrated in vacuo. The residue was purified using a Shimadzu preparative HPLC with a Waters XBridge C8 30×100 mm column and a water (containing 0.1% ammonium hydroxide)-acetonitrile mobile phase. Gradient 25-35% over 10 min.

Workup

  1. stirringThe mixture was stirred at rt for 2 h
  2. customthe layers were separated
  3. extractionThe aqueous phase was extracted with EtOAc
  4. washThe combined organic phases were washed with brine
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified
  8. customover 10 min.

Sources & evidence

ORD record
ord-39cff4f25ab84705b28735f9416dd069
Source dataset
uspto-grants-2012_12
Patent number
US08324239B2

Reaction notes

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